Hydrochloric Acid → HCID 18333054, compound

HRID 2269743Notes

Reaction equation

HRID 2269743 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([C:13]([O:15]CC)=[O:14])[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.Cl>[OH-].[Na+].C1COCC1.CO>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([C:13]([OH:15])=[O:14])[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 18332989HCID 18332989, compound

Product 1

HCID 18333054HCID 18333054, compoundYield 94.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

IN Aqueous sodium hydroxide solution (60 ml) was added dropwise to a mixed solution of ethyl 7-chloro-2-oxo -1,2,3,4-tetrahydro-3-quinolinecarboxylate (14.39 g) in THF (180 ml) and methanol (120 ml) at 0° C. The reaction mixture was stirred at room temperature for 24 hours. 1N Hydrochloric acid (70 ml) was added dropwise to the reaction mixture at 0° C., which was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried and concentrated. The obtained crude crystals were washed with IPE to obtain the entitled compound (12.15 g).

Workup

  1. extractionwhich was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. customdried
  4. concentrationconcentrated
  5. customThe obtained crude crystals
  6. washwere washed with IPE

Sources & evidence

ORD record
ord-14d990032e004c2c9946cfc085e1b792
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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