Sodium Hydroxide → 1-Benzyl-2-methyl-1H-indole-3-carboxylic acid

HRID 2206504Notes

Reaction equation

HRID 2206504 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([O:19]C)=[O:18])=[C:9]1[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1.CO.O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([OH:19])=[O:18])=[C:9]1[CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 102362635methyl 1-benzyl-2-methyl-1H-indole-3-carboxylate

Product 1

HCID 667434811-Benzyl-2-methyl-1H-indole-3-carboxylic acidYield 50%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 1-benzyl-2-methyl-1H-indole-3-carboxylate (446 mg, 1.6 mmol) in tetrahydrofuran (20 mL) and methanol (7 mL) was added sodium hydroxide (320 mg, 8 mmol) in water (7 mL), then stirred at 60° C. for 12 hours. The reaction mixture was concentrated in vacuo and acidified to PH=4 with 6 N hydrochloric acid, collected and dried to give 1-benzyl-2-methyl-1H-indole-3-carboxylic acid as a white solid (212 mg, 50%). LRMS (M+H+) m/z: calcd 265.11. found 265.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customcollected
  3. customdried

Sources & evidence

ORD record
ord-b04824d2d5d14de2ab6f0ba3289f2fb5
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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