Acetic Anhydride → HCID 20427623, compound

HRID 615337Notes

Reaction equation

HRID 615337 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)[N:8]([NH:19][CH3:20])[CH:7]=[C:6]([C:21]([OH:23])=[O:22])[C:5]2=[O:24].[C:25](OC=O)(=[O:27])C.C(OC(=O)C)(=O)C>C(O)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]1)[N:8]([NH:19][CH2:20][CH:25]=[O:27])[CH:7]=[C:6]([C:21]([OH:23])=[O:22])[C:5]2=[O:24]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 55492AmifloxacinHCID 75269Acetic-formic anhydride

Product 1

HCID 20427623HCID 20427623, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

6-Fluoro-methylamino-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid (Example 1) (2.7 g) was added to mixed formic-acetic anhydride prepared from 3.9 g of 96% formic acid and 8.3 g of acetic anhydride. The reaction mixture was stirred at room temperature for 16 hours and then concentrated in vacuo. The solid residue was dissolved in 50 ml of water and the solution made basic with pyridine. The solid product was collected by filtration and recrystallized from acetonitrile to give 2.0 g of 6-fluoro-1-(N-formylmethylamino)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid, cream-colored powder, m.p. 252°-253° C. (decompn.).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe solid residue was dissolved in 50 ml of water
  3. filtrationThe solid product was collected by filtration
  4. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-dec06392b83e465d945bc3bfc8cb5d1b
Source dataset
uspto-grants-1985_02
Patent number
US04499091

Reaction notes

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