Water → 1-(2-Methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid

HRID 1715845Notes

Reaction equation

HRID 1715845 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH2:11][N:12]2[S:15]([C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=2[O:25][CH3:26])(=[O:17])=[O:16])=[CH:7][CH:6]=1)=[O:4].[OH-].[K+].O>CO.O1CCCC1>[CH3:26][O:25][C:19]1[CH:20]=[CH:21][C:22]([CH3:24])=[CH:23][C:18]=1[S:15]([N:12]1[C:13]2[C:8](=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:14]=2)[CH2:9][CH2:10][CH2:11]1)(=[O:16])=[O:17]

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 684326051-(2-Methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid methyl ester

Product 1

HCID 684338071-(2-Methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1-(2-methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid methyl ester (35.09 g, 0.09 mol) in methanol (0.27 L) and tetrahydrofuran (95.00 mL) was treated with a 3N solution of KOH in water (93.00 mL, 0.28 mol) and stirred at room temperature for 18 hours, then at 45° C. for 2 hours. The organic solvents were evaporated and the residual aqueous slurry diluted with water (0.45 L) and cooled to 0° C. The mixture was set to pH 1 with HCl 3N (85.00 mL) and the precipitated solid was filtered and dried under vacuum. 1-(2-Methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid was obtained as an off-white solid, 34.08 g (100%), MS (ISP): m/e=360.1 (M−H).

Workup

  1. waitat 45° C. for 2 hours
  2. customThe organic solvents were evaporated
  3. additionthe residual aqueous slurry diluted with water (0.45 L)
  4. temperaturecooled to 0° C
  5. filtrationthe precipitated solid was filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-6afc0e9b73eb41c6adfbba1f2e138469
Source dataset
uspto-grants-2010_09
Patent number
US07799933B2

Reaction notes

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