Potassium Hydroxide → 2-Chloro-4-{[1-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-benzoic acid

HRID 2235138Notes

Reaction equation

HRID 2235138 reaction equation
[OH-].[K+].C[O:4][C:5](=[O:36])[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[CH:24]=[C:23]3[C:18]([CH2:19][CH2:20][CH2:21][N:22]3[S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=3)(=[O:27])=[O:26])=[CH:17][CH:16]=2)=[O:14])=[CH:8][C:7]=1[Cl:35]>CO.O1CCCC1>[Cl:35][C:7]1[CH:8]=[C:9]([NH:12][C:13]([C:15]2[CH:24]=[C:23]3[C:18]([CH2:19][CH2:20][CH2:21][N:22]3[S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=3)(=[O:27])=[O:26])=[CH:17][CH:16]=2)=[O:14])[CH:10]=[CH:11][C:6]=1[C:5]([OH:36])=[O:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 686978212-Chloro-4-{[1-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-benzoic acid methyl ester

Product 1

HCID 160505222-Chloro-4-{[1-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3 M Potassium hydroxide solution (2 ml) was added to a solution of crude 2-chloro-4-{[1-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-benzoic acid methyl ester (0.097 g, 0.13 mmol) in MeOH (2 ml) and tetrahydrofuran (1 ml) and the mixture stirred for 16 hours. The organic solvent was evaporated and the solution neutralized with 3 M HCl solution (3 ml) forming a white precipitate. The precipitate was filtered and washed with heptane. The solid was then dried under vacuum to give 2-chloro-4-{[1-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-benzoic acid, 0.037 g, as a red solid. LC @215 nm; Rt 2.06: 98%, m/z (ES+): 489.23 (M+H+.); δH (400 MHz; d6-DMSO) 13.18 (1H, br.s), 10.63 (1H, s), 8.22 (1H, d), 8.08 (1H, d), 7.83-7.91 (2H, m), 7.76 (1H, dd), 7.55-7.67 (2H, m), 7.43-7.48 (2H, m), 7.30 (1H, d), 3.84 (2H, m), 2.52 (2H, m), 1.62 (2H, m).

Workup

  1. customThe organic solvent was evaporated
  2. customforming a white precipitate
  3. filtrationThe precipitate was filtered
  4. washwashed with heptane
  5. customThe solid was then dried under vacuum

Sources & evidence

ORD record
ord-27d146d7659f42d1bfd3294abe1468f7
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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