Hydrochloric Acid → HCID 18629328, compound

HRID 1061445Notes

Reaction equation

HRID 1061445 reaction equation
C(O)C.Cl.[CH:5]1([C:8]2[CH:9]=[C:10]([C:48]([O:50]CC)=[O:49])[C:11](=[O:47])[N:12]3[C:17]=2[C:16]([CH3:18])=[C:15]([C:19]2[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=2)[CH2:24][N:23](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:22]4)[CH:14]=[CH:13]3)[CH2:7][CH2:6]1>C1COCC1>[CH:5]1([C:8]2[CH:9]=[C:10]([C:48]([OH:50])=[O:49])[C:11](=[O:47])[N:12]3[C:17]=2[C:16]([CH3:18])=[C:15]([C:19]2[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=2)[CH2:24][NH:23][CH2:22]4)[CH:14]=[CH:13]3)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 18629327HCID 18629327, compound

Product 1

HCID 18629328HCID 18629328, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

8.3 ml of ethanol, 2.8 ml of THF and 1.5 ml of 1N hydrochloric acid were added to 275.4 mg of ethyl 1-cyclopropyl-9-methyl-8-(2-tritylisoindoline-5-yl)-4-oxo-4H-quinolizine-3-carboxylate (I) and the resulting mixture was stirred at 50° C. for 2 hours. The solvent was distilled off under reduced pressure and water was added to the resulting residue and the resulting residue was washed with ethyl acetate, and thereafter, the resulting water layer was concentrated under reduced pressure. 30 ml of water, 10 ml of ethanol and 5 ml of 1N sodium hydroxide were added to the resulting residue and the resulting mixture was stirred at 50° C. for 3.5 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 120.0 mg of 1-cyclopropyl-9-methyl-8-(isoindoline-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
  3. washthe resulting residue was washed with ethyl acetate
  4. concentrationthe resulting water layer was concentrated under reduced pressure
  5. addition30 ml of water, 10 ml of ethanol and 5 ml of 1N sodium hydroxide were added to the resulting residue
  6. stirringthe resulting mixture was stirred at 50° C. for 3.5 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-0b1cf6086e184310bbe363c1c5bb7405
Source dataset
uspto-grants-2003_02
Patent number
US06525066B2

Reaction notes

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