Dimethylformamide → Quinoxaline-6-carbonyl chloride

HRID 1865430Notes

Reaction equation

HRID 1865430 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:17])=O.CN(C=O)C>C1C=CC=CC=1>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([Cl:17])=[O:13])=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 674813Quinoxaline-6-carboxylic acid

Product 1

HCID 2776328Quinoxaline-6-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of quinoxaline-6-carboxylic acid (438 mg, 2.51 mmol) in benzene (16 mL) was added oxalyl chloride (0.26 mL, 3.02 mmol) and anhydrous DMF (0.1 mL). The reaction was stirred at room temperature for 30 minutes after which the mixture was concentrated in vacuo. The resulting yellow solid was azeotroped 3× with toluene and the product was used immediately without further purification.

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe resulting yellow solid was azeotroped 3× with toluene
  3. customthe product was used immediately without further purification

Sources & evidence

ORD record
ord-58a0509e660f4cfd85a32b98168102bb
Source dataset
uspto-grants-2009_12
Patent number
US07625938B2

Reaction notes

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