Methyl 1H-indole-2-carboxylate → 1H-Indole-2-carboxamide

HRID 1677802Notes

Reaction equation

HRID 1677802 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12]CC)=O.[NH:15]1C2C(=CC=CC=2)C=C1C(OC)=O.CO.C(Cl)Cl>N(C)C.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH2:15])=[O:12]

Participants

5

Reactant 3

HCID 70992Methyl 1H-indole-2-carboxylateHCID 73125Ethyl indole-2-carboxylateHCID 21226129Dichloromethane methanol

Product 1

HCID 5948321H-Indole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 27521Dimethylamine, hydrateSolvent

Procedure

Stir ethyl indole-2-carboxylate 1 (X═H, 4.67 mmol) or methyl indole-2-carboxylate 2 (X═H, 4.67 mmol) in Me2NH/H2O (50 mL, 40%). Stir the reaction mixture at rt for 16 h monitoring by tlc (10% MeOH/CH2Cl2). Concentrate the mixture to minimum volume, dilute with H2O and collect the solid by filtration. Wash the filter cake with H2O and dry under vacuum at 60° C. to provide dimethyl amide 4 (X═H, R2═R3=Me), tlc Rf=0.65 (silica gel, 10% MeOH/CH2Cl2).

Workup

  1. concentrationConcentrate the mixture to minimum volume
  2. additiondilute with H2O
  3. customcollect the solid
  4. filtrationby filtration
  5. washWash the filter cake with H2O
  6. customdry under vacuum at 60° C.

Sources & evidence

ORD record
ord-5cf1339349a242329cde0bc10fdf331b
Source dataset
uspto-grants-2011_08
Patent number
US08008340B2

Reaction notes

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