Methylamine → HCID 22164809, compound

HRID 1722253Notes

Reaction equation

HRID 1722253 reaction equation
B(F)(F)F.CCOCC.[Cl:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[O:27])[C:16]([C:22](OCC)=[O:23])=[CH:17][N:18]2[CH3:21])=[CH:13][CH:12]=1.[CH3:28][NH2:29]>>[Cl:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[O:27])[C:16]([C:22]([NH:29][CH3:28])=[O:23])=[CH:17][N:18]2[CH3:21])=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 6329Methylamine3×HCID 8000Boron trifluoride etherate3×HCID 11471099HCID 11471099, compound

Product 1

HCID 22164809HCID 22164809, compound

Procedure

Boron trifluoride etherate (5 ml) was added cautiously to a mixture of ethyl 7-chloro-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate (5 g) and a solution of methylamine in IMS (32%; 35 ml) and the mixture was boiled under reflux for 8 hours. The same quantities of boron trifluoride etherate and methylamine in IMS were added and the mixture was boiled under reflux for 24 hours. The same quantities of boron trifluoride etherate and methylamine in IMS were added and the mixture was boiled under reflux for 8 hours. The mixture was kept at ambient temperature for 16 hours and then filtered. The residue was washed with IMS, dried and recrystallised from aqueous IMS to give the novel compound 7-chloro-1,N-dimethyl-4-oxo-1,4-dihydroquinoline-3-carboxamide, m.p. 260°-263°.

Workup

  1. temperatureunder reflux for 8 hours
  2. temperatureunder reflux for 24 hours
  3. temperatureunder reflux for 8 hours
  4. filtrationfiltered
  5. washThe residue was washed with IMS
  6. customdried
  7. customrecrystallised from aqueous IMS

Sources & evidence

ORD record
ord-cc12b82b24014392ae19d8723c49d2a7
Source dataset
uspto-grants-1989_08
Patent number
US04855291

Reaction notes

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