Water → HCID 12797263, compound

HRID 2412633Notes

Reaction equation

HRID 2412633 reaction equation
[C:1]([C:20]1[C:28]2[C:23](=[CH:24][C:25]([C:29]([O:31]C)=[O:30])=[CH:26][CH:27]=2)[NH:22][CH:21]=1)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH-].[Na+].O>CO>[C:1]([C:20]1[C:28]2[C:23](=[CH:24][C:25]([C:29]([OH:31])=[O:30])=[CH:26][CH:27]=2)[NH:22][CH:21]=1)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 12799951HCID 12799951, compound

Product 1

HCID 12797263HCID 12797263, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-(n-octadecanoyl)indole-6-carboxylate (35.2 g) in methanol (1620 ml), containing sodium hydroxide (32 g) and water (49 ml), was stirred and refluxed for 2 hours. The solution was cooled to room temperature and the solid was collected. The solid was suspended in water (500 ml) and aqueous hydrochloric acid (20 ml, of strength 36% w/v) was added to the suspension with rapid stirring. The solid was collected and was recrystallised from glacial acetic acid to give 3-(n-octadecanoyl)indole-6-carboxylic acid (28 g), in the form of a white solid, m.p. 268°-270° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. customthe solid was collected
  3. additionaqueous hydrochloric acid (20 ml, of strength 36% w/v) was added to the suspension with rapid stirring
  4. customThe solid was collected
  5. customwas recrystallised from glacial acetic acid

Sources & evidence

ORD record
ord-bff40e446f1340258f56ce27d8584c56
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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