Ammonia → HCID 178422933, compound

HRID 1650171Notes

Reaction equation

Cl.[OH:2][C:3]1[C:8]([C:9]([NH2:11])=[O:10])=[C:7]([CH3:12])[C:6]([CH2:13][C:14]2[N:15]=[CH:16][NH:17][CH:18]=2)=[CH:5][CH:4]=1.OC1C(C(OCC)=O)=C(C)C(CC2N=CNC=2)=CC=1.N>>[OH:2][C:3]1[C:8]([C:9]([NH2:11])=[O:10])=[C:7]([CH3:12])[C:6]([CH2:13][C:14]2[N:15]=[CH:16][NH:17][CH:18]=2)=[CH:5][CH:4]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 178422934HCID 178422934, compound

HCID 178470030HCID 178470030, compound

Product 1

HCID 178422933HCID 178422933, compoundYield 61%

Procedure

6-hydroxy-3-[(1H-imidazol-4-yl)methyl]-2-methylbenzamide hydrochloride. A solution of 6.1 g (23.4 mmoles) of ethyl 6-hydroxy-3-[(1H-imidazol-4-yl)methyl]-2-methylbenzoate (prepared in Example 1.C.4.) in 400 ml of liquid ammonia, is heated in an autoclave at 60° C. for 72 hours. The mixture is then evaporated under reduced pressure and the residue is purified by chromatography on silica gel (eluent: 80:20:0.5 v/v/v ethyl acetate-ethanol-ammonia). 3.3 g of 6-hydroxy-3-[(1H-imidazol-4-yl)methyl]-2-methylbenzamide are obtained. Yield: 61%. The amide, treated in ethanol with 1.1 equivalent of hydrochloric acid, is converted into the hydrochloride. Yield: 66% (after recrystallization from water). M.P.: 262.8° C.

Workup

customThe mixture is then evaporated under reduced pressure
customthe residue is purified by chromatography on silica gel (eluent: 80:20:0.5 v/v/v ethyl acetate-ethanol-ammonia)

Sources & evidence

ORD record: ord-b86dd80558a840f5b8711bc77b44b4ff
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04923865

Reaction notes

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