Potassium Hydroxide → 4-(Benzyloxy)-6-methylindole-2-carboxylic Acid

HRID 903925Notes

Reaction equation

HRID 903925 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:19]([O:21]CC)=[O:20])[NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:19]([OH:21])=[O:20])[NH:13]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 23335518Ethyl 4-(benzyloxy)-6-methyl-1H-indole-2-carboxylate

Product 1

HCID 219043124-(Benzyloxy)-6-methylindole-2-carboxylic AcidYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

31.0 4-benzyloxy-2-ethoxycarbonyl-6-methyl indole (see preparation of the primary products in connection with Example 1) are heated to boiling in a mixture of 100 ml ethanol and 100 ml water during addition of 7.0 potassium hydroxide, for 2 to 3 hours. The ethanol is then evaporated in vacuum and the remaining, water alkaline solution is acidified with conc. hydrochloric acid. The resulting precipitate is aspirated, thoroughly washed with water and dried. There is obtained 27.6 g (~95% of theory) 4-benzyloxy-2-carboxy-6-methyl indole; m.p. 178°-180° C.

Workup

  1. custompreparation of the primary products in connection with Example 1)
  2. temperatureare heated
  3. customThe ethanol is then evaporated in vacuum
  4. washthoroughly washed with water
  5. customdried

Sources & evidence

ORD record
ord-26c714820cd14c3caadd591155259e34
Source dataset
uspto-grants-1980_10
Patent number
US04229464

Reaction notes

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