Formaldehyde → 1,4-dihydro-2H-isoquinolin-3-one

HRID 2236404Notes

Reaction equation

HRID 2236404 reaction equation
[C:1]1([CH2:7][C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[P+](O[P+](O)=O)=O.C=O.[C:20](=O)([O-])[O-].[K+].[K+]>>[CH2:20]1[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[CH2:7][C:8](=[O:9])[NH:10]1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 7680BenzeneacetamideHCID 11430Potassium CarbonateHCID 6326976Diphosphonic acid

Product 1

HCID 904691,4-dihydro-2H-isoquinolin-3-oneYield 21%

Conditions

Temperature
155 °C

Procedure

A mixture of phenylacetamide (5 g, 37 mmol), pyrophosphonic acid (80 g, 449.5 mmol) and paraformaldehyde (1.22 g, 40.7 mmol) is heated at 155° C. for 1 h to give a viscous black solution. It is poured into ice water and treated with potassium carbonate to pH 7. The solution is extracted with ethyl acetate, and the organic solution is washed with saturated potassium carbonate, dried over magnesium sulfate, and evaporated to dryness to give 1.145 g (21%) of the product as a yellow solid; MS (ESI) m/z 148.0 (M+1). [Ref: Heterocycles 26(9), 2385 (1987)].

Workup

  1. customto give a viscous black solution
  2. extractionThe solution is extracted with ethyl acetate
  3. washthe organic solution is washed with saturated potassium carbonate
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-cb7d7cb000854b9f8e4e37d29b67de46
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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