Hydrochloric Acid → HCID 18629339, compound

HRID 1061444Notes

Reaction equation

HRID 1061444 reaction equation
C(O)C.Cl.[CH:5]1([C:8]2[CH:9]=[C:10]([C:50]([O:52]CC)=[O:51])[C:11](=[O:49])[N:12]3[C:17]=2[C:16]([O:18][CH3:19])=[C:15]([C:20]2[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=2)[CH:25]([CH3:29])[N:24](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:23]4)[CH:14]=[CH:13]3)[CH2:7][CH2:6]1>C1COCC1>[CH:5]1([C:8]2[CH:9]=[C:10]([C:50]([OH:52])=[O:51])[C:11](=[O:49])[N:12]3[C:17]=2[C:16]([O:18][CH3:19])=[C:15]([C:20]2[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=2)[CH:25]([CH3:29])[NH:24][CH2:23]4)[CH:14]=[CH:13]3)[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 18629326HCID 18629326, compound

Product 1

HCID 18629339HCID 18629339, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.0 ml ethanol, 2.0 ml of THF and 1.0 ml of 1N hydrochloric acid were added to 248.0 mg of ethyl 1-cyclopropyl-9-methoxy-8-(1-methyl-2-tritylisoindoline-5-yl)-4-oxo-4H-quinolizine-3-carboxylate (XIV) and the resulting mixture was stirred at a room temperature for 30 minutes. The solvent was distilled off under reduced pressure and water was added to the resulting residue, which was washed with ethyl acetate, and thereafter, the resulting water layer was concentrated under reduced pressure. 10 ml of water, 5 ml of ethanol and 3 ml of 1N sodium hydroxide were added to the residue and the resulting mixture was stirred at 50° C. for 3 hours. The reaction solution was concentrated under reduced pressure, and thereafter, dissolved in 4 ml of water and neutralized with 1N hydrochloric acid. The precipitated crystal was separated by filtering to obtain 99.1 mg of 1-cyclopropyl-9-methoxy-8-(1-methylisoindoline-5-yl)-4-oxo-4H-quinolizine-3-carboxylic acid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure and water
  2. additionwas added to the resulting residue, which
  3. washwas washed with ethyl acetate
  4. concentrationthe resulting water layer was concentrated under reduced pressure
  5. addition10 ml of water, 5 ml of ethanol and 3 ml of 1N sodium hydroxide were added to the residue
  6. stirringthe resulting mixture was stirred at 50° C. for 3 hours
  7. concentrationThe reaction solution was concentrated under reduced pressure
  8. dissolutiondissolved in 4 ml of water and neutralized with 1N hydrochloric acid
  9. customThe precipitated crystal was separated
  10. filtrationby filtering

Sources & evidence

ORD record
ord-05238b429778445f9e0e89b3952a64fc
Source dataset
uspto-grants-2003_02
Patent number
US06525066B2

Reaction notes

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