Pyridine → Benzamide, N-(5-chloro-2-hydroxy-4-nitrophenyl)-

HRID 1252388Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].N1C=CC=CC=1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[C:19]([NH:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Reactant 3

HCID 1049Pyridine

HCID 7412Benzoyl chloride

HCID 38948482-Amino-4-chloro-5-nitrophenol

Product 1

HCID 5483228Benzamide, N-(5-chloro-2-hydroxy-4-nitrophenyl)-Yield 89%

Procedure

188 (1 mole) g of 2-amino-4-chloro-5-nitrophenol and 79 g (1 mole) of pyridine were added to 500 ml of N-dimethylacetamide, followed by dropping 140 g (1 mole) of benzoyl chloride at about 5° C. in about 30 minutes and agitating for further 30 minutes. The resulting crystals were filtered and washed with 500 ml of methanol to obtain 260 g (yield 89%) of an isomer of exemplified compound [IV]-(1) (2-benzamido-4-chloro-5-nitrophenol). From the melting point of below 250° C. and an IR spectrum (νC=O, 1654 cm-1), this compound was found to be 2-benzamide compound.

Workup

customat about 5° C.
customin about 30 minutes
filtrationThe resulting crystals were filtered
washwashed with 500 ml of methanol

Sources & evidence

ORD record: ord-4e4c8ccb5fe54b3eba624e781073023a
Source dataset: uspto-grants-1988_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04743595

Reaction notes

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