Dimethylformamide → 1-Ethyl-6-fluoro-7-[3-(methylaminomethyl)pyrrolidin-1-yl]-4-oxo-quinoline-3-carboxylic acid

HRID 622475Notes

Reaction equation

HRID 622475 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10](F)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2].CN(C)C=O.[CH3:24][NH:25][CH2:26][CH:27]1[CH2:31][CH2:30][NH:29][CH2:28]1>C(#N)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10]([N:29]3[CH2:30][CH2:31][CH:27]([CH2:26][NH:25][CH3:24])[CH2:28]3)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8005211-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 13491795N-Methyl-1-(pyrrolidin-3-yl)methanamine

Product 1

HCID 4659331-Ethyl-6-fluoro-7-[3-(methylaminomethyl)pyrrolidin-1-yl]-4-oxo-quinoline-3-carboxylic acidYield 85.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.00 g (3.95 mmole) 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 10 ml N,N-dimethylformamide, 75 ml acetonitrile, and 1.35 g (11.85 mmole) of N-methyl-3-pyrrolidinemethanamine were refluxed overnight The reaction was cooled to room temperature and filtered. The precipitate was washed with water, ethanol/ether (1:3), and finally with ether until dry to give 1.17 g of 1-ethyl-6-fluoro-1,4-dihydro-7-[3-[(methylamino)methyl]-1-pyrrolidinyl]-4-oxo-3-quinolinecarboxylic acid, mp 247°-250° C.

Workup

  1. temperaturewere refluxed overnight The reaction
  2. filtrationfiltered
  3. washThe precipitate was washed with water, ethanol/ether (1:3)
  4. dry with materialfinally with ether until dry

Sources & evidence

ORD record
ord-6638d86546a14f3985f5e29aad15489b
Source dataset
uspto-grants-1988_09
Patent number
US04771054

Reaction notes

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