Hydrochloric Acid → 1-Cyclopropyl-8-(difluoromethoxy)-7-(1-methyl-2,3-dihydro-1H-isoindol-5-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 377294Notes

Reaction equation

HRID 377294 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:18]4[CH:19]=[C:20]5[C:24](=[CH:25][CH:26]=4)[CH:23]([CH3:27])[N:22](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH2:21]5)[C:12]=3[O:14][CH:15]([F:17])[F:16])[C:7](=[O:47])[C:6]([C:48]([O:50]CC)=[O:49])=[CH:5]2)[CH2:3][CH2:2]1.Cl>C(O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:18]4[CH:19]=[C:20]5[C:24](=[CH:25][CH:26]=4)[CH:23]([CH3:27])[NH:22][CH2:21]5)[C:12]=3[O:14][CH:15]([F:17])[F:16])[C:7](=[O:47])[C:6]([C:48]([OH:50])=[O:49])=[CH:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15887920HCID 15887920, compound

Product 1

HCID 4799301-Cyclopropyl-8-(difluoromethoxy)-7-(1-methyl-2,3-dihydro-1H-isoindol-5-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 91.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 4 ml of ethanol was suspended 1.00 g of ethyl (-)-1-cyclopropyl-8-difluoromethoxy-7-(1-methyl-2-tritylisoindolin-5-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylate, followed by adding thereto 0.26 ml of 6N hydrochloric acid, and the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was filtered, after which 0.75 ml of a 5N aqueous sodium hydroxide solution was added to the filtrate and the resulting mixture was stirred at room temperature for 1 hour. To the reaction mixture was added 16 ml of water, followed by filtration. Carbon dioxide was bubbled into the filtrate and the crystals were collected by filtration to obtain 0.56 g of light-yellow (-)-1-cyclopropyl-8-difluoromethoxy-7-(1-methyl-isoindolin-5-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.

Workup

  1. additionby adding
  2. filtrationThe reaction mixture was filtered
  3. additionafter which 0.75 ml of a 5N aqueous sodium hydroxide solution was added to the filtrate
  4. additionTo the reaction mixture was added 16 ml of water
  5. filtrationfollowed by filtration
  6. customCarbon dioxide was bubbled into the filtrate
  7. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-bbfbfb64f2184b60ad0af4256993f696
Source dataset
uspto-grants-2000_02
Patent number
US06025370

Reaction notes

Loading…