Dichloromethane → HCID 59426170, compound

HRID 506016Notes

Reaction equation

HRID 506016 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]([OH:16])=O)=[CH:4]1)[CH3:2].C(Cl)Cl.C(Cl)(=O)C(Cl)=O.[NH4+:26].[OH-]>CN(C=O)C>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]([NH2:26])=[O:16])=[CH:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 53415958HCID 53415958, compound

Product 1

HCID 59426170HCID 59426170, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Ethyl-6-methoxy-1H-indole-3-carboxylic acid (250 mg, 1.14 mmol) is suspended in a solution of CH2Cl2 (12.5 mL) and DMF (10 μL). Oxalyl chloride (230 μL, 2.64 mmol) is added, and the reaction mixture is stirred for 1 hour at room temperature. This mixture is then slowly poured into a rapidly stirring solution of concentrated NH4OH (5 mL). This is then partitioned in H2O and EtOAc. The residue from the ethyl acetate layer is triturated with acetone to yield 1-ethyl-6-methoxy-1H-indole-3-carboxamide (134 mg, 54%) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-5387b9d2cf8747b6b812b80341742dab
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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