Ammonium Chloride → HCID 18476102, compound

HRID 1384402Notes

Reaction equation

C[Al](C)C.[Cl-].[NH4+:6].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23]CC)=O)=[CH:17][CH:16]=2)=[CH:11][C:10]=1[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=1>C1(C)C=CC=CC=1>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([NH2:6])=[O:23])=[CH:19][CH:20]=2)=[CH:11][C:10]=1[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of trimethylaluminium in toluene (10 mL of 2.0 M) is added over 30 minutes to a stirred suspension of ammonium choride (107 g, 20 mmol) in toluene (20 mL) at 5° C. under an argon atmosphere. The mixture is stirred at 20° C. for 2 h, treated with a solution of 4′-methoxy-3′-(3-nitrophenyl)-[1,1′-biphenyl]-4-carboxylic acid, ethyl ester (1.65 g, 4.3 mmol) in toluene (40 mL) and stirred at 60° C. for 18 h. The cooled mixture is washed with hydrochloric acid (50 mL of 0.5 M) followed by saturated aqueous sodium chloride (50 mL), dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by crystallization from ethyl acetate-t-butylethyl ether to give 4′-methoxy-3′-(3-nitrophenyl)-[1,1′-biphenyl]-4-carboxamide as a colourless crystalline solid, m.p. 201-205° C.

Workup

stirringstirred at 60° C. for 18 h
washThe cooled mixture is washed with hydrochloric acid (50 mL of 0.5 M)
dry with materialdried (Na2SO4)
filtrationfiltered
customthe solvent is evaporated off under reduced pressure
customto yield the crude product which
customis purified by crystallization from ethyl acetate-t-butylethyl ether

Sources & evidence

ORD record: ord-b11a9bec80c04c1087d8939e48ad6e62
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06258843B1

Reaction notes

Loading…