Methanol → Methyl 1-oxo-1,2-dihydroisoquinoline-3-carboxylate

HRID 1020011Notes

Reaction equation

HRID 1020011 reaction equation
[C:1](O)(=O)[CH2:2][NH:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[C:14](CC1C=CC=CC=1C=O)(O)=[O:15].[OH-:26].[K+].[CH3:28][OH:29]>>[O:26]=[C:4]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:1]=[C:2]([C:28]([O:15][CH3:14])=[O:29])[NH:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 866643832-Carboxymethylbenzaldehyde hippuric acid

Product 1

HCID 641183Methyl 1-oxo-1,2-dihydroisoquinoline-3-carboxylateYield 99%

Conditions

Temperature
65 °C

Procedure

The 2-carboxymethylbenzaldehyde hippuric acid adduct from above (1.0 g, 3.3 mmoles) was dissolved in methanol (20 mls) and solid potassium hydroxide (0.37 g, 6.6 mmoles) was added. The clear solution was heated (65° C.) for 1 hour. The reaction was evaporated and the solid residue partitioned between water (25 mls) and ethyl acetate (25 mls). The aqueous layer was further extracted with ethyl acetate (2×10 mls) and the combined ethyl acetate extracts washed with brine (10 mls) water (10 mls). After drying over magnesium sulphate the solution was evaporated to leave a yellow solid (0.68 g, 99% yield).

Workup

  1. customThe reaction was evaporated
  2. customthe solid residue partitioned between water (25 mls) and ethyl acetate (25 mls)
  3. extractionThe aqueous layer was further extracted with ethyl acetate (2×10 mls)
  4. washthe combined ethyl acetate extracts washed with brine (10 mls) water (10 mls)
  5. dry with materialAfter drying over magnesium sulphate the solution
  6. customwas evaporated

Sources & evidence

ORD record
ord-56c1c7c8a4854d16bb6e3ee30938b9b2
Source dataset
uspto-grants-2014_05
Patent number
US08716302B2

Reaction notes

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