1-Cyclopropyl-5,6-difluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid → 5-Amino-1-cyclopropyl-6-fluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 373529Notes

Reaction equation

HRID 373529 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9](F)[C:10]([F:21])=[C:11]([N:14]4[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:23])[C:6]([C:24]([OH:26])=[O:25])=[CH:5]2)[CH2:3][CH2:2]1.[NH3:27].C(O)C>>[NH2:27][C:9]1[C:10]([F:21])=[C:11]([N:14]2[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]2)[CH:12]=[C:13]2[C:8]=1[C:7](=[O:23])[C:6]([C:24]([OH:26])=[O:25])=[CH:5][N:4]2[CH:1]1[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 148802131-Cyclopropyl-5,6-difluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 22020343Ethanol, reaction products with ammonia, distn. residues

Product 1

HCID 148802245-Amino-1-cyclopropyl-6-fluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Procedure

In a sealed tube, 1-cyclopropyl-5,6-difluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid was aminated with ammonia/ethanol as in Example 13 to give 5-amino-1-cyclopropyl-6-fluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxlic acid. m.p 216°-218° C.

Sources & evidence

ORD record
ord-98d6cb2425ca40cd99f10c9bd8f8467b
Source dataset
uspto-grants-1992_11
Patent number
US05164392

Reaction notes

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