Acetic Anhydride → HCID 19593018, compound

HRID 613523Notes

Reaction equation

HRID 613523 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[NH:17][CH3:18])=[O:5].C(O[C:28](=[O:30])[CH3:29])(=O)C>>[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[N:17]([CH3:18])[C:28](=[O:30])[CH3:29])=[O:5]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 19592760HCID 19592760, compound

Product 1

HCID 19593018HCID 19593018, compound

Conditions

Temperature
120 °C

Procedure

A suspension of 8-(2,6-dichlorobenzoylamino)-4-methylaminoquinoline (130 mg) in acetic anhydride (2 ml) was heated at 120° C. for 3 hours. The solvent was removed in vacuo and the residue was dissolved in methanol (3 ml). To a solution was added 1N sodium hydroxide solution (0.5 ml) and the mixture was stirred for 30 minutes. The solvent was removed in vacuo and the residue was washed with hot 50% ethanol (2 ml) and filtered. The residue was washed with hot 95% ethanol (1 ml) and the filtrate was allowed to stand to ambient temperature. The resulting precipitates were collected by filtration and dried to give 8-(2,6-dichlorobenzoylamino)-4-(N-methylacetamido)quinoline (90 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in methanol (3 ml)
  3. additionTo a solution was added 1N sodium hydroxide solution (0.5 ml)
  4. customThe solvent was removed in vacuo
  5. washthe residue was washed with hot 50% ethanol (2 ml)
  6. filtrationfiltered
  7. washThe residue was washed with hot 95% ethanol (1 ml)
  8. customto stand to ambient temperature
  9. customThe resulting precipitates
  10. filtrationwere collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-e5594953ba4242c5b72d1f1b8405da50
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

Loading…