Dichloromethane → HCID 59426369, compound

HRID 907113Notes

Reaction equation

HRID 907113 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:16]([OH:18])=O)=[CH:10][N:11]2[CH2:14][CH3:15])=[CH:7][CH:6]=1)=[O:4].C(Cl)Cl.C(Cl)(=O)C(Cl)=O.[NH4+:28].[OH-]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:16]([NH2:28])=[O:18])=[CH:10][N:11]2[CH2:14][CH3:15])=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 59425724HCID 59425724, compound

Product 1

HCID 59426369HCID 59426369, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Ethyl-1H-indole-3,6-dicarboxylic acid 6-methyl ester (600 mg, 2.43 mmol) was suspended in a solution of CH2Cl2 (27 ml) and DMF (20 μL). Oxalyl chloride (470 μL, 5.38 mmol) was added, and the reaction mixture was stirred for 1 hour at room temperature. This mixture was then slowly poured into a rapidly stirring solution of concentrated NH4OH (10 mL). This was then partitioned in H2O and EtOAc. The residue from the ethyl acetate layer was triturated with acetone to yield 6-methoxycarbonyl-1-ethyl-1H-indole-3-carboxamide (511 mg, 85%) as a white solid.

Workup

  1. customThis was then partitioned in H2O
  2. customThe residue from the ethyl acetate layer was triturated with acetone

Sources & evidence

ORD record
ord-43ecbb2a9b964414acd9ceec5d9ec959
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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