Formic Acid → 1-Cyclopropyl-6-fluoro-8-methoxy-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 2249254Notes

Reaction equation

HRID 2249254 reaction equation
[CH:1](O)=O.C=O.[CH:6]1([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:27])=[C:16]([N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)[C:17]=3[O:19][CH3:20])[C:12](=[O:28])[C:11]([C:29]([OH:31])=[O:30])=[CH:10]2)[CH2:8][CH2:7]1.O>C([O-])=O.[Na+]>[CH:6]1([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:27])=[C:16]([N:21]4[CH2:26][CH2:25][N:24]([CH3:1])[CH2:23][CH2:22]4)[C:17]=3[O:19][CH3:20])[C:12](=[O:28])[C:11]([C:29]([OH:31])=[O:30])=[CH:10]2)[CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 962WaterHCID 465562PD 135042

Product 1

HCID 107382321-Cyclopropyl-6-fluoro-8-methoxy-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 2723810Sodium FormateSolvent

Procedure

In a mixture of sodium formate (22 mg), 87% formic acid (0.3 ml) and 37% formalin (25 μl) and 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid (60 mg) was stirred for 2 hours at 100° to 120° C. After cooling, water (1 ml) was added to the reaction mixture and then concentrated. To the residue was added water (0.5 ml), adjusted to pH 7 with 1N aqueous sodium hydroxide solution and the solution was allowed to stand in a refrigerator. The resulting precipitate was collected by filtration and washed with water to give the title compound (33 mg) as colorless needles, mp 229°-232° C. (decompd.).

Workup

  1. temperatureAfter cooling
  2. concentrationconcentrated
  3. additionTo the residue was added water (0.5 ml)
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-89d5dae3b0794781acf81b009a69e678
Source dataset
uspto-grants-1991_08
Patent number
US05043450

Reaction notes

Loading…