Water → HCID 68435626, compound

HRID 1715835Notes

Reaction equation

HRID 1715835 reaction equation
C[O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][N:11]2[S:14]([C:17]2[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=2)(=[O:16])=[O:15])=[CH:7][CH:6]=1)=[O:4].[OH-].[K+].O>C(O)C>[CH3:24][C:19]1[CH:18]=[C:17]([S:14]([N:11]2[C:12]3[C:8](=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:13]=3)[CH2:9][CH2:10]2)(=[O:16])=[O:15])[CH:22]=[C:21]([CH3:23])[CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 68433630HCID 68433630, compound

Product 1

HCID 68435626HCID 68435626, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

1-(3,5-Dimethyl-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (0.40 g, 1.17 mmol) was suspended in ethanol (2.00 mL) and treated with 3N KOH in water (1.17 mL, 3.51 mmol). The mixture was warmed at 50° C. and stirred for 1 hour, then warmed at 70° C. and stirred for 20 min. After cooling to room temperature, the volatiles were evaporated. The residue was dissolved in water (1.00 mL) and the pH set to 1 with 2N HCl. The precipitate was filtered, washing with water, then dried under high vacuum. 1-(3,5-Dimethyl-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid was obtained as an off-white solid, 0.38 g (98%), MS (ISP): m/e=330.3 (M−H).

Workup

  1. temperaturewarmed at 70° C.
  2. stirringstirred for 20 min
  3. temperatureAfter cooling to room temperature
  4. customthe volatiles were evaporated
  5. dissolutionThe residue was dissolved in water (1.00 mL)
  6. filtrationThe precipitate was filtered
  7. washwashing with water
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-a14d56e2240e4abda5c0ae3a7d3deb83
Source dataset
uspto-grants-2010_09
Patent number
US07799933B2

Reaction notes

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