2-Chloroaniline → HCID 14390295, compound

HRID 621948Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:22]([CH2:23][C:24]([OH:26])=O)[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[N:15]=2)=[CH:10][CH:9]=1.[Cl:27][C:28]1[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=1[NH2:30].C(N(CC)CC)C>CN(C)C=O.O>[Cl:27][C:28]1[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=1[NH:30][C:24](=[O:26])[CH2:23][N:22]1[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:16]2[N:15]=[C:14]1[C:11]1[CH:10]=[CH:9][C:8]([Cl:7])=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Under a nitrogen atmosphere, oxalyl chloride (1.73 g, 0.014 mole) was added slowly to a stirred and chilled (10°-15° C.) suspension of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (3.7 g, 0.013 mole) in 50 ml of dimethylformamide. The reaction mixture was heated at 60° C. for 5 hours. The solution of the acyl chloride prepared above was added dropwise under nitrogen atmosphere to a stirred and chilled (10°-15° C.) solution of o-chloroaniline (1.79 g, 0.014 mole), triethylamine (1.42 g, 0.014 mole), and 75 ml of dimethylformamide. After the addition, the reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was poured into 200 ml of water. The crystalline solid was collected by filtration, washed with ater, and dried under high vacuum overnight to give 2.76 g (54%) of crystals, mp 232°-235.5° C.

Workup

temperaturechilled
additionabove was added dropwise under nitrogen atmosphere to
stirringa stirred
additionAfter the addition
stirringto stir at room temperature overnight
filtrationThe crystalline solid was collected by filtration
washwashed with ater
customdried under high vacuum overnight

Sources & evidence

ORD record: ord-5c8c82ab4d2e4b68a195b1095f30ee65
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04824951

Reaction notes

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