1-Cyclopropyl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 14304602, compound
Reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([F:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.[NH2:22][C:23]1([CH3:28])[CH2:27][CH2:26][NH:25][CH2:24]1>C(#N)C>[NH2:22][C:23]1([CH3:28])[CH2:27][CH2:26][N:25]([C:11]2[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[C:9]([F:17])[C:10]=2[F:16])[CH2:24]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.8 g), 3-amino-3-methylpyrrolidine (0.8 g), and acetonitrile (35 ml) was stirred at 50° C. for 30 minutes. The precipitated crystals were collected by filtration, and washed with water. The crystals were dissolved in 10% aqueous ammonia, treated with activated carbon, and concentrated under reduced pressure. The precipitated crystals were collected by filtration, washed with water and dried to give 7-(3-amino-3-methyl-1-pyrrolidinyl)-1-cyclopropyl-5,6,8-trifluoro-1,4-dihydro-4-oxoquinoline 3-carboxylic acid (0.81 g), m.p. 280°-282° C.
Workup
- filtrationThe precipitated crystals were collected by filtration
- washwashed with water
- dissolutionThe crystals were dissolved in 10% aqueous ammonia
- additiontreated with activated carbon
- concentrationconcentrated under reduced pressure
- filtrationThe precipitated crystals were collected by filtration
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-d3c98f0e8b554348996f44df8259e46d
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04886810
Reaction notes
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