Formaldehyde → 1-Cyclopropyl-7-(3-cyclopropyl-4-methyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 2165700Notes

Reaction equation

HRID 2165700 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:23])=[C:11]([N:14]4[CH2:19][CH2:18][NH:17][CH:16]([CH:20]5[CH2:22][CH2:21]5)[CH2:15]4)[CH:12]=3)[C:7](=[O:24])[C:6]([C:25]([OH:27])=[O:26])=[CH:5]2)[CH2:3][CH2:2]1.[CH2:28]=O>C(O)=O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:23])=[C:11]([N:14]4[CH2:19][CH2:18][N:17]([CH3:28])[CH:16]([CH:20]5[CH2:21][CH2:22]5)[CH2:15]4)[CH:12]=3)[C:7](=[O:24])[C:6]([C:25]([OH:27])=[O:26])=[CH:5]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 14839412HCID 14839412, compound

Product 1

HCID 230429671-Cyclopropyl-7-(3-cyclopropyl-4-methyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 210 mg of 1-cyclopropyl-7-(3-cyclopropyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.24 ml of 37% formaldehyde and 0.30 ml of 90% formic acid was heated at 100° C. for 4 hours, then allowed to cool and the excess reagents removed under reduced pressure. Water was added and the pH adjusted to 7 with 1N sodium hydroxide. The mixture was then extracted several times with chloroform:methanol (95:5), the extracts combined, dried, filtered and evaporated. The resulting oil was triturated with ether, giving 170 mg of the desired product.

Workup

  1. temperatureto cool
  2. customthe excess reagents removed under reduced pressure
  3. additionWater was added
  4. extractionThe mixture was then extracted several times with chloroform:methanol (95:5)
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting oil was triturated with ether

Sources & evidence

ORD record
ord-73de8de8b51f4d6db5ed75b68372bfd1
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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