Methyl 4-Formylbenzoate → HCID 69891371, compound

HRID 1840878Notes

Reaction equation

HRID 1840878 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][CH:4]=1)=O.[CH2:13]([N:19]1[C:28]2[C:23](=[CH:24][C:25]([C:29](=[O:31])[CH3:30])=[CH:26][CH:27]=2)[C:22]([CH3:33])([CH3:32])[CH2:21][C:20]1=[O:34])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>[OH-].[Na+].CO>[CH2:13]([N:19]1[C:28]2[C:23](=[CH:24][C:25]([C:29](=[O:31])[CH:30]=[CH:1][C:3]3[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=3)=[CH:26][CH:27]=2)[C:22]([CH3:33])([CH3:32])[CH2:21][C:20]1=[O:34])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 15294Methyl 4-FormylbenzoateHCID 121354162(1H)-Quinolinone, 6-acetyl-1-hexyl-3,4-dihydro-4,4-dimethyl-2×

Product 1

HCID 69891371HCID 69891371, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 4-formylbenzoate (22 mg, 13.4 mmol) was added to a solution of N-hexyl-6-acetyl 4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one (Intermediate 6a, 40 mg, 13.3 mmol) in 2 mL of 1 N NaOH and 4 mL of methanol. After stirring at room temperature for 18 h, the reaction mixture was extracted with ethyl acetate (3×10 mL). The combined organic layer was washed with brine (1×10 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chormatography (50:49:1 hexane/ethyl acetate/acetic acid) gave the title compound as a light yellow solid (18.9 mg, 33% yield).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (3×10 mL)
  2. washThe combined organic layer was washed with brine (1×10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated at reduced pressure
  5. customPurification by flash chormatography (50:49:1 hexane/ethyl acetate/acetic acid)

Sources & evidence

ORD record
ord-2607ea74d60c44acae5afca76d7ae594
Source dataset
uspto-grants-2004_01
Patent number
US06683092B1

Reaction notes

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