Hydrochloric Acid → HCID 18333029, compound

HRID 2269747Notes

Reaction equation

HRID 2269747 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH:17]([C:23]([O:25]CC)=[O:24])[C:18](=[O:22])[NH:19]2)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.[OH-].[Na+].Cl>[Cl-].[Na+].CO>[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH:17]([C:23]([OH:25])=[O:24])[C:18](=[O:22])[NH:19]2)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 18332948HCID 18332948, compound

Product 1

HCID 18333029HCID 18333029, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 5234Sodium ChlorideSolvent

Procedure

To a solution of ethyl 7-benzyloxycarbonylamino-2-oxo-1,2,3,4-tetrahydro-3-quinolinecarboxylate (7.8 g) in a mixed solvent of THF (80 ml) and methanol (80 ml) was added 1N aqueous sodium hydroxide (32 ml) under 10° C. The reaction mixture was stirred at room temperature for 4 hours, to which was added 1N hydrochloric acid (35 ml) under 1° C. The reaction mixture was diluted with a saturated aqueous sodium chloride solution and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried, and concentrated to obtain the entitled compound (7.20 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fe583aa21bb840f0806fc81481365930
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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