Formaldehyde → 1-Ethyl-6,8-difluoro-1,4-dihydro-7-(8-methyl-6,8-diazabicyclo[3.2.2]non-6-yl)-4-oxo-3-quinolinecarboxylic acid

HRID 981740Notes

Reaction equation

HRID 981740 reaction equation
[CH:1]12[NH:27][CH2:26][CH:5]([N:6]([C:8]3[C:17]([F:18])=[C:16]4[C:11]([C:12](=[O:24])[C:13]([C:21]([OH:23])=[O:22])=[CH:14][N:15]4[CH2:19][CH3:20])=[CH:10][C:9]=3[F:25])[CH2:7]1)[CH2:4][CH2:3][CH2:2]2.[CH2:28]=O>C(O)=O>[CH2:19]([N:15]1[C:16]2[C:11](=[CH:10][C:9]([F:25])=[C:8]([N:6]3[CH2:7][CH:1]4[N:27]([CH3:28])[CH2:26][CH:5]3[CH2:4][CH2:3][CH2:2]4)[C:17]=2[F:18])[C:12](=[O:24])[C:13]([C:21]([OH:23])=[O:22])=[CH:14]1)[CH3:20]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 15085937HCID 15085937, compound

Product 1

HCID 150859381-Ethyl-6,8-difluoro-1,4-dihydro-7-(8-methyl-6,8-diazabicyclo[3.2.2]non-6-yl)-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 0.20 g (0.52 mmol) of 7-(6,8-diazabicyclo[3.2.2]non-6-yl)-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 5 ml of 37% formaldehyde solution, and 5 ml of formic acid was heated under reflux for 3.6 hr. The reaction mixture was evaporated to dryness and the residue was suspended in ethanol/HCl. The solid was collected by filtration to give 0.16 g of the title compound as the hydrochloride salt, mp ≤300°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3.6 hr
  3. customThe reaction mixture was evaporated to dryness
  4. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-9a11450a175a48b2b7e905679e8e5cca
Source dataset
uspto-grants-1991_02
Patent number
US04992546

Reaction notes

Loading…