Oxalyl chloride → HCID 59424944, compound

HRID 505992Notes

Reaction equation

HRID 505992 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12](O)=[O:13])=[CH:9][CH:10]=2)[N:5]([CH2:15][CH3:16])[CH:4]=1)#[N:2].C(Cl)(=O)C([Cl:20])=O>C(Cl)Cl.CN(C=O)C>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([Cl:20])=[O:13])=[CH:9][CH:10]=2)[N:5]([CH2:15][CH3:16])[CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 59425917HCID 59425917, compound

Product 1

HCID 59424944HCID 59424944, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 3-cyano-1-ethyl-1H-indole-6-carboxylic acid (0.42 g, 1.96 mmol) in CH2Cl2 (15 mL) is cooled to 0° C. The suspension is treated with DMF (2 drops) and then oxalyl chloride (0.34 mL, 3.92 mmol) is added via syringe during 2 minutes after which the ice bath is removed and the reaction mixture is allowed to warm to ambient temperature during 1.5 h during which time the reaction becomes a yellow solution. The solution is then concentrated in vacuo to afford 0.46 g (quantitative yield) of 3-cyano-1-ethyl-1H-indole-6-carbonyl chloride as a yellow solid.

Workup

  1. customis removed
  2. temperatureto warm to ambient temperature during 1.5 h during which time the reaction
  3. concentrationThe solution is then concentrated in vacuo

Sources & evidence

ORD record
ord-2115d6df555b4ed4b8f11209b1a3d87f
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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