2-Bromo-1-(3-nitrophenyl)ethan-1-one → 2-hydroxy-1-(3-nitrophenyl)-1-ethanone

HRID 1446991Notes

Reaction equation

HRID 1446991 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7](=[O:10])[CH2:8]Br)([O-:3])=[O:2].C([O-])(=[O:16])C.[Na+]>C(O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7](=[O:10])[CH2:8][OH:16])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 752132-Bromo-1-(3-nitrophenyl)ethan-1-oneHCID 517045Sodium Acetate

Product 1

HCID 27638542-hydroxy-1-(3-nitrophenyl)-1-ethanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Reaction of m-nitrophenacyl bromide with sodium acetate in ethanol gave m-nitrophenacyl alcohol. This was treated with dicyandiimide and HCl in aqueous methanol to give 2-guanidino4-(3-nitrophenyl)oxazole hydrochloride, m.p. 250°-251° C. The nitro residue was reduced with iron powder in acetic acid containing 10% v/v water to give 2-guanidino-4-(3-aminophenyl)oxazole.

Sources & evidence

ORD record
ord-76393fb21dc544dc81e2e90c203d7641
Source dataset
uspto-grants-1982_02
Patent number
US04315009

Reaction notes

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