Methanol → methyl 1H-indole-4-carboxylate

HRID 1058344Notes

Reaction equation

HRID 1058344 reaction equation
N1C2C(=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=2)C=C1.Cl.CN(C)[CH2:16][CH2:17][CH2:18][N:19]=[C:20]=NCC.[CH3:25]O>ClCCl>[CH3:25][O:12][C:10]([C:7]1[C:6]2[CH:5]=[CH:20][NH:19][C:18]=2[CH:17]=[CH:16][CH:8]=1)=[O:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 5952301H-indole-6-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 2733668methyl 1H-indole-4-carboxylateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-Dimethylaminopyridine (7.6 mg, 0.06 mmol) was added to a mixture of 1H-indole-6-carboxylic acid (100 mg, 0.62 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (131 mg, 0.68 mmol) and methanol (1 mL, 24.7 mmol) in dichloromethane (2 mL). The mixture was allowed to stir at room temperature overnight, then the solvent was evaporated and ethyl acetate (20 mL) was added. The solution was washed with 1N hydrochloric acid solution (2×15 mL), saturated sodium bicarbonate solution (15 mL) and brine (10 mL), dried (MgSO4), filtered and evaporated in vacuo to give 1H-indole-4-carboxylic acid methyl ester (85.4 mg, 79% yield) as a pale yellow solid.

Workup

  1. customthe solvent was evaporated
  2. additionethyl acetate (20 mL) was added
  3. washThe solution was washed with 1N hydrochloric acid solution (2×15 mL), saturated sodium bicarbonate solution (15 mL) and brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-dcccc8c8291d45638dbdfcc01d48e5bb
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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