Ammonia → HCID 69958639, compound

HRID 369333Notes

Reaction equation

HRID 369333 reaction equation
[NH2:1][C:2]1[C:3]([F:28])=[CH:4][C:5]([F:27])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15](F)[C:16]=3[Cl:18])[C:11](=[O:21])[C:10]([C:22](OCC)=[O:23])=[CH:9]2)[CH:7]=1.[NH3:29].C[N:31](C)C=O>>[NH2:29][C:15]1[C:16]([Cl:18])=[C:17]2[C:12]([C:11](=[O:21])[C:10]([C:22]([NH2:31])=[O:23])=[CH:9][N:8]2[C:6]2[CH:7]=[C:2]([NH2:1])[C:3]([F:28])=[CH:4][C:5]=2[F:27])=[CH:13][C:14]=1[F:20]

Participants

4

Reactant 3

HCID 222Ammonia2×HCID 6228DimethylformamideHCID 23284675HCID 23284675, compound

Product 1

HCID 69958639HCID 69958639, compound

Conditions

Temperature
50 °C

Procedure

Ethyl 1-(5-amino-2,4-difluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (200 mg) was dissolved in N,N-dimethylformamide (4 ml). 28% Aqueous ammonia (1 ml) was added to this solution, and the mixture was stirred overnight at 50° C. in a closed state. Additional 28% aqueous ammonia (2 ml) was added, and the mixture was stirred overnight in the same manner as described above. After the temperature of the reaction mixture was given back to room temperature, it was concentrated to two-thirds under reduced pressure. Red solids deposited were collected by filtration, washed with water and then dried to obtain the title compound (90 mg) as a reddish brown powder.

Workup

  1. stirringthe mixture was stirred overnight in the same manner
  2. customwas given back to room temperature
  3. concentrationit was concentrated to two-thirds under reduced pressure
  4. filtrationRed solids deposited were collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-6c41e611de834d1997461acd8a6ae408
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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