Sodium Hydroxide → 3-Amino-6-fluoro-2-(4-chlorophenyl)-4-quinolinecarboxylic acid

HRID 1073272

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[OH-:13].[Na+].Cl.[NH2:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)=O>O.C(O)C.O1CCCC1>[NH2:16][C:17]1[C:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[N:7][C:8]2[C:4]([C:5]=1[C:6]([OH:11])=[O:13])=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2

Participants

Conditions

Temperature: 85 °C

Procedure

To a stirred suspension of 7 g of 5-fluoroisatin in 58 ml of water was added a solution of 9.36 g of sodium hydroxide in 33 ml of water. The solution was heated to 85° C. and a solution of 12 g of 2-amino-1-(4-chlorophenyl)ethanone hydrochloride in a mixture of 92 ml of ethanol and 40 ml of tetrahydrofuran and 92 ml of water was added drop-wise over 2 hours. After the addition was complete, the solution was refluxed for an additional 30 minutes and then the ethanol and tetrahydrofuran were removed by distillation. The mixture was cooled to 20° C. and filtered through celite. The filtrate was acidified to pH 4 with acetic acid. The solid was filtered off, washed with water and dried, giving 12.8 g of the desired compound as a yellow solid, mp 241°-243° C.

Workup

additionwas added drop-wise over 2 hours
additionAfter the addition
temperaturethe solution was refluxed for an additional 30 minutes
customthe ethanol and tetrahydrofuran were removed by distillation
temperatureThe mixture was cooled to 20° C.
filtrationfiltered through celite
filtrationThe solid was filtered off
washwashed with water
customdried

Sources & evidence

ORD record: ord-5dcee6d70101433ebcaa9e230850c4b0
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04968702

Linked notes

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