Hydrochloric Acid → 7-(benzyloxy)-1H-indole-2-carboxylic acid

HRID 1762941Notes

Reaction equation

HRID 1762941 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:5])C.[OH-].[Na+].Cl>O1CCCC1.CO>[CH2:16]([O:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:14]2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13242189Ethyl 7-(benzyloxy)-1h-indole-2-carboxylate

Product 1

HCID 132421927-(benzyloxy)-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-benzyloxyindole-2-carboxylic acid ethyl ester in 600 ml of tetrahydrofuran and 200 ml of methanol is combined with 500 ml of 2N sodium hydroxide solution and stirred for 3 hours at room temperature. The reaction mixture is then acidified under ice cooling with 10% hydrochloric acid and extracted twice with ethyl acetate. The combined organic phases are dried, treated with active carbon, and concentrated. The residue is recrystallized from toluene, thus producing 35 g of 7-benzyloxyindole-2-carboxylic acid, mp 166°-168° C.

Workup

  1. extractionextracted twice with ethyl acetate
  2. customThe combined organic phases are dried
  3. additiontreated with active carbon
  4. concentrationconcentrated
  5. customThe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-0683743783254d79b789438005c81107
Source dataset
uspto-grants-1989_05
Patent number
US04835175

Reaction notes

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