Oxalyl chloride → 1H-indole-2-carbonyl Chloride

HRID 1838099Notes

Reaction equation

HRID 1838099 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]([OH:12])=O.C(Cl)(=O)C([Cl:16])=O>CN(C=O)C.C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([Cl:16])=[O:12]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 72899Indole-2-carboxylic acid

Product 1

HCID 118162081H-indole-2-carbonyl Chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of indole-2-carboxylic acid (960 mg, 6.0 mmol), 10 mL CH2Cl2 and 2 drops DMF under argon at 0° C., was added oxalyl chloride (2.68 mL, 24.0 mmol) dropwise. The reaction was stirred at 23° C. for 3.5 hours and then concentrated in vacuo to yield a yellow oil which was taken on to the next step without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. customto yield a yellow oil which
  3. customwas taken on to the next step without further purification

Sources & evidence

ORD record
ord-fc41af56902b42ddb076a9137235d399
Source dataset
uspto-grants-2004_01
Patent number
US06673788B2

Reaction notes

Loading…