Acetohydroxamic Acid → 1,2-Benzoxazol-3-amine

HRID 2089128Notes

Reaction equation

HRID 2089128 reaction equation
[OH:1][NH:2][C:3](=O)[CH3:4].C[C:7]([O-])([CH3:9])[CH3:8].[K+].[C:12](O[Na])([CH3:15])(C)C.C(O[K])CCC.C[N:25]1C(=O)CCC1>CS(C)=O.CN(C=O)C>[NH2:25][C:3]1[C:4]2[CH:12]=[CH:15][CH:8]=[CH:7][C:9]=2[O:1][N:2]=1

Participants

8

Reactant 5

HCID 1990Acetohydroxamic AcidHCID 13387N-methyl-2-pyrrolidoneHCID 23665647Potassium tert-butoxideHCID 178418730sodium 2-methylpropan-2-olateHCID 178454393potassium butan-1-olate

Product 1

HCID 27797491,2-Benzoxazol-3-amine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

Commercially available N-hydroxy-acetamide (XVI) is reacted with a suitable substituted fluorobenzonitrile (III), in the presence of an organic base such as t-BuOK, t-BuONa or n-BuOK, in an organic solvent such as DMF, DMSO or NMP, at a temperature in the range of about 80° C. to about 120° C., to yield the corresponding amino-benzoisoxazole (XVII). Amino-bezoisoxazole (XVII) is reacted with glyoxylic acid (V), in the presence of a reducing reagent such as NaBH4, NaBH3CN or NaBH(OAc)3, in an organic solvent such as MeOH, EtOH or IPA with catalytic amount of acid such as acetic acid, trifluoroacetic acid or formic acid, at a temperature in the range of 25° C. to about 60° C., to yield the corresponding acid (XVIII).

Sources & evidence

ORD record
ord-a3e41cb4495643fe8c45b67f78c5347a
Source dataset
uspto-grants-2013_05
Patent number
US08436023B2

Reaction notes

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