Homophthalic anhydride → 1(2H)-Isoquinolinone, 3-butyl-

HRID 373133Notes

Reaction equation

HRID 373133 reaction equation
[C:1]1(=O)[O:7][C:5](=O)[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]2[CH2:2]1.[C:13](Cl)(=O)[CH2:14][CH2:15][CH2:16]C.[OH-].[NH4+:21]>N1C=CC=CC=1.C(Cl)(Cl)Cl>[CH2:13]([C:1]1[NH:21][C:5](=[O:7])[C:4]2[C:3]([CH:2]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 12801Homophthalic anhydrideHCID 14923Ammonium HydroxideHCID 61186Valeryl chloride

Product 1

HCID 64512411(2H)-Isoquinolinone, 3-butyl-

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 4 g (24 mmol) of homophthalic anhydride in 12 ml of dry pyridine in a 250 L 3 neck flask fitted with a reflux condenser and addition funnel at 0° C. was added 5.4 g (45 mmol) of valeryl chloride in 16 ml of dry chloroform over 45 minutes. The reaction mixture was stirred for a further 1 hour and then was treated with 100 ml of conc. ammonium hydroxide dropwise. The mixture was refluxed for 2 hours and then allowed to stand overnight at room temperature. The two phases were separated and the organic phase was washed with water (1×20 ml). The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The residue was recrystallized from hot MeOH/water to give a pale purple solid.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. waitto stand overnight at room temperature
  3. customThe two phases were separated
  4. washthe organic phase was washed with water (1×20 ml)
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystallized from hot MeOH/water
  9. customto give a pale purple solid

Sources & evidence

ORD record
ord-9adc9aff516f4265b596cfc01ad307fb
Source dataset
uspto-grants-1992_11
Patent number
US05162340

Reaction notes

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