Formaldehyde → 1-Ethyl-6-fluoro-7-[3-[(hexyloxy)methyl]-4-methyl-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 248510Notes

Reaction equation

HRID 248510 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:27])=[C:10]([N:13]3[CH2:18][CH2:17][NH:16][CH:15]([CH2:19][O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:14]3)[CH:11]=2)[C:6](=[O:28])[C:5]([C:29]([OH:31])=[O:30])=[CH:4]1)[CH3:2].[CH2:32]=O>C(O)=O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:27])=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH3:32])[CH:15]([CH2:19][O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:14]3)[CH:11]=2)[C:6](=[O:28])[C:5]([C:29]([OH:31])=[O:30])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 148393921-Ethyl-6-fluoro-7-[3-[(hexyloxy)methyl]-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 148393931-Ethyl-6-fluoro-7-[3-[(hexyloxy)methyl]-4-methyl-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A 400 mg portion of 1-ethyl-6-fluoro-7-[3-[(hexyloxy)methyl]-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid was added to a mixture of 1.2 ml of 37% formaldehyde and 1.5 ml of 90% formic acid. The mixture was heated on a steam bath for one hour, evaporated to an oil, diluted with 5 ml of water and neutralized with 1N sodium hydroxide. The solid was collected and dried, giving 360 mg of the desired product, mp 172°-174° C.

Workup

  1. temperatureThe mixture was heated on a steam bath for one hour
  2. customevaporated to an oil
  3. additiondiluted with 5 ml of water and neutralized with 1N sodium hydroxide
  4. customThe solid was collected
  5. customdried

Sources & evidence

ORD record
ord-90059609741e4d7f8d3514f4691ec0ac
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

Loading…