Dimethylformamide → 1H-Indole-3-carbonyl chloride

HRID 61962

Reaction equation

HRID 61962 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[CH:2]1.CN(C)C=O.C(Cl)(=O)C([Cl:21])=O>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([Cl:21])=[O:12])=[CH:2]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chloride2×HCID 69867Indole-3-Carboxylic Acid

Product 1

HCID 123802781H-Indole-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

Next, a solution of indole-3-carbonyl chloride was prepared. A well-stirred suspension of indole-3-carboxylic acid (67.7 mg, 0.42 mmol) in dry DCM (2 ml) containing a small amount of dimethylformamide (DMF) (20 μL) was treated with oxalyl chloride (0.84 mmol, 107 mg, 72 μL) at 0° C. Following addition to the oxalyl chloride, the mixture was stirred for 20 minutes at 23° C., producing a clear, slightly yellow solution. This solution was evaporated to dryness in vacuo at 0.1 Torr to ensure removal of excess oxalyl chloride, and was subsequently re-dissolved in 2 ml of dry DCM.

Workup

  1. customproducing a clear, slightly yellow solution
  2. customThis solution was evaporated to dryness in vacuo at 0.1 Torr
  3. customremoval of excess oxalyl chloride
  4. dissolutionwas subsequently re-dissolved in 2 ml of dry DCM

Sources & evidence

ORD record
ord-820bf830bd7040b0b9ca890ad376d2e0
Source dataset
uspto-grants-2016_09
Patent number
US09445596B2

Linked notes

Loading…