Thionyl Chloride → Quinoxaline-6-carbonyl chloride

HRID 1071573Notes

Reaction equation

HRID 1071573 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.O=S(Cl)[Cl:16]>>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([Cl:16])=[O:13])=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 674813Quinoxaline-6-carboxylic acid

Product 1

HCID 2776328Quinoxaline-6-carbonyl chloride

Conditions

Temperature
80 °C

Procedure

A suspension of quinoxaline-6-carboxylic acid (1.8 g, 10.3 mmole) (Chem. Ber. 1953, 86, 1295) in SOCl2 (30 ml) was stirred at 80° C. for 3 h. The resulting yellow solution was concentrated by distillation, and the residue treated with toluene and concentrated to dryness in vacuo giving a pale beige solid (2.0 g, quant.). m/z [ESMS]: 203 [M+EtOH−Cl]+.

Workup

  1. concentrationThe resulting yellow solution was concentrated by distillation
  2. additionthe residue treated with toluene
  3. concentrationconcentrated to dryness in vacuo
  4. customgiving a pale beige solid (2.0 g, quant.)

Sources & evidence

ORD record
ord-fc164ffce5e04d0fbdf15a9eb0c94742
Source dataset
uspto-grants-2005_06
Patent number
US06906089B2

Reaction notes

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