Formaldehyde → 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-methyl-3-(2-furanyl)-1-piperazinyl]-3-quinolinecarboxylic acid

HRID 248520Notes

Reaction equation

HRID 248520 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:25])=[C:11]([N:14]4[CH2:19][CH2:18][NH:17][CH:16]([C:20]5[O:21][CH:22]=[CH:23][CH:24]=5)[CH2:15]4)[CH:12]=3)[C:7](=[O:26])[C:6]([C:27]([OH:29])=[O:28])=[CH:5]2)[CH2:3][CH2:2]1.[CH2:30]=O>C(O)=O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:25])=[C:11]([N:14]4[CH2:19][CH2:18][N:17]([CH3:30])[CH:16]([C:20]5[O:21][CH:22]=[CH:23][CH:24]=5)[CH2:15]4)[CH:12]=3)[C:7](=[O:26])[C:6]([C:27]([OH:29])=[O:28])=[CH:5]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 148394021-Cyclopropyl-6-fluoro-7-[3-(2-furanyl)-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 148394131-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-methyl-3-(2-furanyl)-1-piperazinyl]-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 200 mg of 1-cyclopropyl-6-fluoro-7-[3-(2-furanyl)-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.3 ml of 90% formic acid and 0.24 ml of 37% formalin was heated for 2 hours, then evaporated. The residue was diluted with water, neutralized to pH 7 with 1N sodium hydroxide, the solid collected and washed with water, methanol and ether and dried in vacuo, giving 145 mg of the desired product, mp 122°-124° C.

Workup

  1. temperaturewas heated for 2 hours
  2. customevaporated
  3. additionThe residue was diluted with water
  4. customthe solid collected
  5. washwashed with water, methanol and ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-8ed45fb7fa814223b875067325111ece
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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