Potassium Hydroxide → HCID 16050815, compound

HRID 2235167Notes

Reaction equation

HRID 2235167 reaction equation
C([O:3][C:4](=[O:36])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:22]=[C:21]3[C:17]([CH2:18][CH2:19][N:20]3[S:23]([C:26]3[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=3[O:33][CH3:34])(=[O:25])=[O:24])=[C:16]([CH3:35])[CH:15]=2)=[O:13])=[CH:7][CH:6]=1)C.[OH-].[K+]>C(O)C>[Cl:32][C:30]1[CH:29]=[CH:28][C:27]([O:33][CH3:34])=[C:26]([S:23]([N:20]2[C:21]3[C:17](=[C:16]([CH3:35])[CH:15]=[C:14]([C:12]([NH:11][C:8]4[CH:9]=[CH:10][C:5]([C:4]([OH:36])=[O:3])=[CH:6][CH:7]=4)=[O:13])[CH:22]=3)[CH2:18][CH2:19]2)(=[O:25])=[O:24])[CH:31]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68699430HCID 68699430, compound

Product 1

HCID 16050815HCID 16050815, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 4-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-4-methyl-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid ethyl ester (185 mg, 0.350 mmol) in ethanol (2 mL) and 3 M aq. potassium hydroxide solution (0.35 mL, 1.05 mmol) was heated at 50° C. for 18 h, then volatile material was removed by distillation. The residue was taken up in water (2 mL) and brought to pH 1 by addition of 2 M aq. hydrochloric acid solution. The precipitate was collected by filtration and dried, producing 4-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-4-methyl-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid (139 mg, 76%). Off-white solid, MS (ISP): m/e 499.1 (M−H).

Workup

  1. customvolatile material was removed by distillation
  2. additionbrought to pH 1 by addition of 2 M aq. hydrochloric acid solution
  3. filtrationThe precipitate was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-1d19c94f6ce04bab88067a73149bb3e5
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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