5-(Aminomethyl)-1,2-oxazol-3-ol (Muscimol) [Isotopes] [C4H6N2O2]

5-(Aminomethyl)-1,2-oxazol-3-ol (Muscimol) [C4H6N2O2]

Query Query HO

Results

Date

10 reactions in Reaxys

2018-08-03 18h:21m:06s (UTC)

N O

1. Query NH 2

Search as: Product, As drawn, No mixtures ) AND (IDE.RN='2763-96-4') AND (IDE.INCHI='ZJQHPWUVQPJPQTUHFFFAOYSA-N') NOT (RX.RXRN=606417))

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5-(Aminomethyl)-1,2-oxazol-3-ol (Muscimol) [C4H6N2O2]

O O

N NH 2

O

HO

N O

N NH 2

I HO

NH 2

I

Rx-ID: 46033477 View in Reaxys 1/10 Yield

Conditions & References

19 %

With hydrogen bromide, acetic acid, Time= 17h, T= 60 °C , Inert atmosphere Abdul Manan, Mohd Abdul Fatah; Cordes, David B.; Slawin, Alexandra M. Z.; Bühl, Michael; Liao, Vivian W. Y.; Chua, Han. C.; Chebib, Mary; O'Hagan, David; Chemistry - A European Journal; vol. 23; nb. 45; (2017); p. 10848 - 10852 View in Reaxys

N

HO

N

O

O O

NH 2

NH 2

Rx-ID: 890544 View in Reaxys 2/10 Yield

Conditions & References With DOWEX W50x8-200 mesh (H+-form), hydrogen bromide in acetic acid, Time= 0.25h, Heating

62 %

Pevarello; Varasi; Synthetic Communications; vol. 22; nb. 13; (1992); p. 1939 - 1948 View in Reaxys With hydrogen bromide in acetic acid, Time= 0.166667h, Heating Krogsgaard-Larsen,P.; Christensen,S.B.; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol.

30; (1976); p. 281-282percent View in Reaxys

N

HO

N

O

O O

Cl

H

NH 2

NH 2

Rx-ID: 2768971 View in Reaxys 3/10 Yield

Conditions & References

64 %

With hydrogen bromide in acetic acid, Time= 0.166667h, Heating Chiarino, D.; Napoletano, M.; Sala, A.; Tetrahedron Letters; vol. 27; nb. 27; (1986); p. 3181 - 3182 View in Reaxys

HO

N

HO

N O

O

Cl

NH 2

Rx-ID: 1394780 View in Reaxys 4/10 Yield 34 %

Conditions & References With ammonia in water, T= 60 - 80 °C Konda; Takahashi; Onda; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1083 - 1087 View in Reaxys With ammonium hydroxide Frater-Schroeder,M. et al.; Helvetica Chimica Acta; vol. 52; (1969); p. 720 - 724 View in Reaxys

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5-(Aminomethyl)-1,2-oxazol-3-ol (Muscimol) [C4H6N2O2]

O

N

HO

N

O

O O N

NH 2 O O

Rx-ID: 2567265 View in Reaxys 5/10 Yield

Conditions & References

38 %

With borane-THF in tetrahydrofuran, Time= 21.5h, Ambient temperature Oster, Timothy A.; Harris, Thomas M.; Journal of Organic Chemistry; vol. 48; nb. 23; (1983); p. 4307 - 4311 View in Reaxys N

HO

N

HO

O

O Cl

H

NH 2

NH 2

Rx-ID: 2601896 View in Reaxys 6/10 Yield

Conditions & References

51 %

With ion exchanger (Lewatit S 100 G1) in water Jaeger; Frey; Liebigs Annalen der Chemie; vol. No. 4; (1982); p. 817 - 820 View in Reaxys N

HO

O

N

HO

O

NH

NH 2

OH

O

Rx-ID: 2976124 View in Reaxys 7/10 Yield

Conditions & References With hydrogenchloride, dimethylsulfide borane complex, 1.) THF, rwflux, 22 h, 2.) 2 h; reflux, 1 h, Yield given. Multistep reaction Welch, W. M.; Synthetic Communications; vol. 12; nb. 14; (1982); p. 1089 - 1091 View in Reaxys

O

HO

N O

N

O

NH 2

O

Br

Rx-ID: 3256727 View in Reaxys 8/10 Yield

Conditions & References With ammonium hydroxide, Dowex 50W-X2 (H-form), 1.) EtOH, RT, 1 h, 2.) H2O, Yield given. Multistep reaction Nakamura, Norio; Tajima, Yawara; Sakai, Kiyoshi; Heterocycles; vol. 17; (1982); p. 235 - 245 View in Reaxys

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2018-08-03 18:22:54

5-(Aminomethyl)-1,2-oxazol-3-ol (Muscimol) [C4H6N2O2]

HO

HO

N O

N

HO

N O

O OH NH

Cl

NH 2

N O

Rx-ID: 3758003 View in Reaxys 9/10 Yield

Conditions & References

10 %, 65 %

With ammonia in methanol, Time= 5h, T= 50 °C McCarry; Savard; Tetrahedron Letters; vol. 22; nb. 51; (1981); p. 5153 - 5156 View in Reaxys

HO

N O

NH 2

Rx-ID: 5931301 View in Reaxys 10/10 Yield

Conditions & References Urethan XV, Ba(OH)2 Nakamura,N.; Chemical and Pharmaceutical Bulletin; vol. 19; (1971); p. 46 - 51 View in Reaxys Decarboxilierung von Saeure I Nakamura,N.; Chemical and Pharmaceutical Bulletin; vol. 19; (1971); p. 46 - 51 View in Reaxys 3-benzyloxy-cpd. (III), hydrogenolyse Patent; Gagneux et al.; CH443300; (1964); ; vol. 69; nb. 106697x; (1968) View in Reaxys 3-bromo-5-bromomethyl-cpd.(II); 1)NH3, 2)MeOH/alcali Patent; Gagneux et al.; CH443301; (1964); ; vol. 69; nb. 106697x; (1968) View in Reaxys 3-methoxy-cpd.(IV), HCl Patent; Gagneux et al.; CH443301; (1964); ; vol. 69; nb. 106697x; (1968) View in Reaxys 3-hydroxy-isoxazole-5-carbamide, B2H6 Patent; Gagneux; Haflinger; US3397209; (1966); ; vol. 69; nb. 106696w; (1968) View in Reaxys 3-Hydroxy-5-chlormethylisoxazol III, NH3 Patent; Geigy; CH443302; (1964); ; vol. 69; nb. 67367t; (1968) View in Reaxys 5-Azidomethylderivat IV, H2 Patent; Geigy; CH443298; (1964); ; vol. 69; nb. 67364q; (1968) View in Reaxys Isoxazol II, HCl Patent; Geigy, I.R., AG; CH443303; (1964); ; vol. 69; nb. 43904q; (1968) View in Reaxys Amanita muscaria (als Abbauprodukt von Ibotensaeure (I))

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5-(Aminomethyl)-1,2-oxazol-3-ol (Muscimol) [C4H6N2O2]

Eugster et al.; Tetrahedron Letters; (1965); p. 1813 View in Reaxys 3-Methoxy-5-aminomethyl-isoxazol (3), Hydrolyse Gagneux,A.R. et al.; Tetrahedron Letters; (1965); p. 2077 - 2079 View in Reaxys /BRN= 742193/, Ammoniak Gagneux,A.R. et al.; Tetrahedron Letters; (1965); p. 2077 - 2079 View in Reaxys

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