Oxalyl chloride → HCID 90858244, compound

HRID 599501Notes

Reaction equation

HRID 599501 reaction equation
[C:1]([C:3](=[CH:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:9]=1)[C:4](O)=[O:5])#[N:2].C(Cl)(=O)C([Cl:26])=O>ClCCl.CN(C=O)C>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([CH:7]=[C:3]([C:4]([Cl:26])=[O:5])[C:1]#[N:2])=[CH:9]1)[CH3:22]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 67273507HCID 67273507, compound

Product 1

HCID 90858244HCID 90858244, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 2-cyano-3-(1-ethoxycarbonylmethyl-1H-indol-3-yl)-acrylic acid (3.0 g, 10 mmol) in dry dichloromethane (120 ml), in the presence of a few drops of dry DMF, was added oxalyl chloride (1.7 ml, 20 mmol). After stirring at rt overnight, the volatiles were removed under reduced pressure, the residue azeotoped twice with dry toluene and dried in vacuo, affording crude title compound (3.18 g) in quantitative yield. This material was stored under argon and was used without further purification.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customdried in vacuo

Sources & evidence

ORD record
ord-35931fe472674880b7f25d8408d8c542
Source dataset
uspto-grants-2011_03
Patent number
US07897788B2

Reaction notes

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