Acetic Acid → Methyl 1-oxo-1,2-dihydroisoquinoline-3-carboxylate

HRID 2365257Notes

Reaction equation

HRID 2365257 reaction equation
[N+:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[C-].[CH:8]([C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([O:14]C)=O)=O.[H-].[Na+].C(O)(=O)C>CN(C)C=O.O>[O:14]=[C:12]1[C:11]2[C:10](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=[C:3]([C:4]([O:6][CH3:7])=[O:5])[NH:1]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 243003Methyl 2-formylbenzoateHCID 547815Methyl isocyanoacetate

Product 1

HCID 641183Methyl 1-oxo-1,2-dihydroisoquinoline-3-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of methyl isocyanoacetate (4.20 mL, 46.2 mmol) and methyl 2-formylbenzoate (6.90 g, 42.0 mmol) in 30 mL of N,N-dimethylformamide was added dropwise to a suspension of sodium hydride (1.21 g, 50.4 mmol) in 20 mL of N,N-dimethylformamide. After 5 hr, the mixture was treated with 10% aqueous acetic acid and water and extracted 2× with ethyl acetate. The combined organic extracts were washed 3× with water and brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was crystallized from 1:10 ethyl acetate:hexanes to provide methyl 1-oxo-1,2-dihydroisoquinoline-3-carboxylate.

Workup

  1. extractionextracted 2× with ethyl acetate
  2. washThe combined organic extracts were washed 3× with water and brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from 1:10 ethyl acetate

Sources & evidence

ORD record
ord-e18a183112344399ba325258864fc3d1
Source dataset
uspto-grants-2014_04
Patent number
US08697690B2

Reaction notes

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