Hydrochloric Acid → HCID 71556167, compound

HRID 1497040Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12]([N+:22]([O-:24])=[O:23])=[CH:11][CH:10]=2)=[O:5])C.[OH-].[K+].Cl.[CH2:29]([OH:31])[CH3:30]>O>[CH2:29]([O:31][C:7]1[C:6]([C:4]([OH:5])=[O:3])=[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:22]([O-:24])=[O:23])[CH:13]=2)[N:8]=1)[CH3:30]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-chloro-6-nitro-4-phenyl-quinoline-3-carboxylic acid ethyl ester (10 mg, 0.028 mmol) was suspended in ethanol and treated with 3N KOH (0.1 ml, 10.7 Eq). The mixture was warmed to 80° C. for 24 h, then further 3N KOH (0.1 ml, 10.7 Eq.) was added and stirring at 80° C. was continued for further 24 h. The mixture was diluted with water and acidified to pH 1 with HCl 1N. The slurry was extracted with dichloromethane and the extracts were evaporated to yield the title compound (7.6 mg, 82%) as a white powder. MS (ESI): 339.2 (M+H)+.

Workup

extractionThe slurry was extracted with dichloromethane
customthe extracts were evaporated

Sources & evidence

ORD record: ord-f49f74a89ad142f49ca607b1d29941a6
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199938B2

Reaction notes

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