Hydrochloric Acid → HCID 22266516, compound

HRID 1994260Notes

Reaction equation

HRID 1994260 reaction equation
C[O:2][C:3]([C:5]1[C:6](=[O:19])[N:7]([CH2:15][CH2:16][CH2:17][CH3:18])[C:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=2[CH:14]=1)=[O:4].[OH-].[Na+].Cl>C(O)C>[CH2:15]([N:7]1[C:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=2[CH:14]=[C:5]([C:3]([OH:4])=[O:2])[C:6]1=[O:19])[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14449901HCID 14449901, compound

Product 1

HCID 22266516HCID 22266516, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Butyl-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid methyl ester (1-015-02) (263 mg, 1 mmol) was dissolved in ethanol (6 mL), and to the reaction mixture was added an aqueous solution of sodium hydroxide (2 mol/L, 0.6 mL, 1.2 mmol), and the reaction mixture was stirred at room temperature for 30 min. To the reaction mixture was added diluted hydrochloric acid (0.4 N, 6 mL) and the reaction mixture was extracted with ethyl acetate (25 mL). To the aqueous layer was added sodium chloride, followed by extraction with ethyl acetate (25 mL), and the combined organic layers were dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The obtained crystal residue was recrystallized from hexane to give 1-butyl-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid (4-002-01) (220 mg, 88%) as a white crystal.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (25 mL)
  2. additionTo the aqueous layer was added sodium chloride
  3. extractionfollowed by extraction with ethyl acetate (25 mL)
  4. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe obtained crystal residue was recrystallized from hexane

Sources & evidence

ORD record
ord-ebfd689aa125444ea7886ab347e2ee22
Source dataset
uspto-grants-2010_01
Patent number
US07652141B2

Reaction notes

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