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Hydrochloric Acid → 1-Cyclohexylmethyl-3-methyl-1H-indole-6-carboxylic acid

HRID 380425
Notes
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Reaction equation

HRID 380425 reaction equation
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19]C)=[O:18])[CH:15]=3)[C:10]([CH3:21])=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Li+].Cl>CO>[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=3)[C:10]([CH3:21])=[CH:9]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 22663183methyl 1-cyclohexylmethyl-3-methyl-1H-indole-6-carboxylate

Product 1

HCID 226633891-Cyclohexylmethyl-3-methyl-1H-indole-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 1-cyclohexylmethyl-3-methyl-1 H-indole-6-carboxylate and lithium hydroxide (8.0 g) in aqueous methanol (300 ml, 1:2, v/v) was heated at 70° C. for 4 hours. The reaction mixture was cooled to room temperature, then acidified by addition of dilute hydrochloric acid and then extracted three times with ethyl acetate (150 ml). The combined extracts were dried over sodium sulphate then evaporated to give the title compound as a white solid (7.3 g). M+271.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted three times with ethyl acetate (150 ml)
  3. dry with materialThe combined extracts were dried over sodium sulphate
  4. customthen evaporated

Sources & evidence

ORD record
ord-c1fc3af61252420191acb87d4635dbb1
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06303600B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes