Acetic Anhydride → 2-acetamidopropyl-4-phenyl-1(2H)-isoquinolone

HRID 326024Notes

Reaction equation

HRID 326024 reaction equation
[NH2:1][CH:2]([CH3:21])[CH2:3][N:4]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:20].[C:22](OC(=O)C)(=[O:24])[CH3:23]>C(O)(=O)C>[C:22]([NH:1][CH:2]([CH3:21])[CH2:3][N:4]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:20])(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 132699402-(2-aminopropyl)-4-phenyl-1(2H)-isoquinolone

Product 1

HCID 132699442-acetamidopropyl-4-phenyl-1(2H)-isoquinoloneYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5 g of 2-(2-aminopropyl)-4-phenyl-1(2H)-isoquinolone, 10 ml of acetic anhydride and 10 ml of glacial acetic acid was warmed on a water bath for 3 hours and the resulting reaction mixture was poured into ice-water. The precipitated crystals were extracted with dichloromethane, and the extract was thoroughly washed successively with a 5% aqueous solution of sodium hydroxide and water, and then dried over anhydrous sodium sulfate. The crystals obtained by distilling off the solvent was recrystallized from ethanol to obtain 4.8 g (83% yield) of 2-(2-acetamidopropyl-4-phenyl-1(2H)-isoquinolone having a melting point of 177° C. as colorless needles.

Workup

  1. temperaturewas warmed on a water bath for 3 hours
  2. customthe resulting reaction mixture
  3. extractionThe precipitated crystals were extracted with dichloromethane
  4. washthe extract was thoroughly washed successively with a 5% aqueous solution of sodium hydroxide and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe crystals obtained
  7. distillationby distilling off the solvent
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-4619d624609c42ffb9f4c9180c8fd1a0
Source dataset
uspto-grants-1984_04
Patent number
US04443607

Reaction notes

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