Acetic Acid → HCID 22461266, compound

HRID 1937621Notes

Reaction equation

HRID 1937621 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:10][C:9]2[NH:8][C:7]([C:11]([O:13]CC)=[O:12])=[C:6]([CH2:16][CH3:17])[C:5]=2[C:4](=[O:18])[CH2:3]1.[OH-].[K+].C(O)(=O)C>CCO.O>[CH3:19][C:2]1([CH3:1])[CH2:10][C:9]2[NH:8][C:7]([C:11]([OH:13])=[O:12])=[C:6]([CH2:16][CH3:17])[C:5]=2[C:4](=[O:18])[CH2:3]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 22461293HCID 22461293, compound

Product 1

HCID 22461266HCID 22461266, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of ethyl 6,6-dimethyl-3-ethyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate (5.4 g, 0.02 mol) and KOH (2.9 g, 0.05 mol) in EtOH (25 mL) and water (7.5 mL) was heated at reflux for 6 h. The mixture was cooled to 60° C., and neutralized by the addition of acetic acid. Water (80 mL) was added and the cream precipitate collected by filtration. The precipitate was washed with EtOH and hexane then dried under vacuum at 50° C. The acid (4 g, 83%) was isolated as a cream solid, and used without further purification. mp>198° C. 1H NMR (360 MHz, d6-DMSO δ 1.00 (6H,s), 1.04 (3H,t,J=7.3 Hz), 2.22 (2H,s), 2.62 (2H,s), 2.98 (2H,q,J=7.3 Hz), 11.72 (1H, br s). C13H17NO3. O.4(H2O) requires: C, 64.39; H, 7.40; N, 5.73%. Found:C, 64.38, H, 7.30; N, 5.70%. MS(ES+) 236 (M+1).

Workup

  1. temperatureat reflux for 6 h
  2. filtrationthe cream precipitate collected by filtration
  3. washThe precipitate was washed with EtOH and hexane
  4. customthen dried under vacuum at 50° C

Sources & evidence

ORD record
ord-63d2f5c8582f4d6fb24dc80101df807d
Source dataset
uspto-grants-2002_05
Patent number
US06395766B1

Reaction notes

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