Hydrochloric Acid → HCID 15622511, compound

HRID 1722301Notes

Reaction equation

HRID 1722301 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:29])=[C:11]([N:15]4[CH2:19][CH2:18][CH:17]([N:20]([CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH3:21])[CH2:16]4)[C:12]=3[CH3:14])[C:7](=[O:30])[C:6]([C:31]([O:33]CC)=[O:32])=[CH:5]2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>>[CH2:22]([N:20]([CH:17]1[CH2:18][CH2:19][N:15]([C:11]2[C:12]([CH3:14])=[C:13]3[C:8]([C:7](=[O:30])[C:6]([C:31]([OH:33])=[O:32])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[CH:9][C:10]=2[F:29])[CH2:16]1)[CH3:21])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14834672HCID 14834672, compound

Product 1

HCID 15622511HCID 15622511, compoundYield 39.5%

Procedure

To ethyl 1-cyclopropyl-7-[3-(N-benzyl-N-methylamino)-1-pyrrolidinyl]-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (0.86 g) is added 10% aqueous sodium hydroxide (7 ml), and the mixture is refluxed for 5 hours. After cooling, the mixture is acidified with diluted hydrochloric acid and is extracted with dichloromethane. The aqueous layer is adjusted to about pH 7.5 with sodium hydrogen carbonate, and the resulting precipitates are recrystallized from ethanol-diethyl ether to give 7-[3-(N-benzyl-N-methylamino)-1-pyrrolidinyl]-1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.32 g), as pale yellow powder, m.p. 160.8°-161.3° C.

Workup

  1. temperaturethe mixture is refluxed for 5 hours
  2. temperatureAfter cooling
  3. extractionis extracted with dichloromethane
  4. customthe resulting precipitates
  5. customare recrystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-5f254afdb47e406b95d650204a13ae6a
Source dataset
uspto-grants-1989_08
Patent number
US04855292

Reaction notes

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