Acetic Acid → 2-(2-aminopropyl)-4-phenyl-1(2H)-isoquinolone

HRID 326021Notes

Reaction equation

HRID 326021 reaction equation
C([NH:8][CH:9]([CH3:28])[CH2:10][N:11]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:27])C1C=CC=CC=1.C(O)(=O)C.[H][H]>[C].[Pd].C(O)C>[NH2:8][CH:9]([CH3:28])[CH2:10][N:11]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:27]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 13305504HCID 13305504, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 132699402-(2-aminopropyl)-4-phenyl-1(2H)-isoquinoloneYield 75.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

36.8 g of 2-(2-benzylaminopropyl)-4-phenyl-1(2H)-isoquinolone preapred as described above, 12 g of 5% palladium-carbon, 50 ml of glacial acetic acid and 200 ml of ethanol were mixed, and the mixture was catalytically reduced while introducing hydrogen gas into the mixture at 60° to 70° C. After completion of the reduction reaction, the mixture was filtered, and the solvent was distilled off from the filtrate. The resulting residue was dissolved in 5% hydrochloric acid and the solution was washed with ethyl acetate. The aqueous layer was separated and rendered neutral with a 10% aqueous solution of sodium hydroxide. The resulting precipitate was filtered and recrystallized from a mixture of ethyl acetate and petroleum ether to obtain 20.9 g (75% yield) of 2-(2-aminopropyl)-4-phenyl-1(2H)-isoquinolone having a melting point of 104° C. as colorless prisms.

Workup

  1. additionwere mixed
  2. customAfter completion of the reduction reaction
  3. filtrationthe mixture was filtered
  4. distillationthe solvent was distilled off from the filtrate
  5. dissolutionThe resulting residue was dissolved in 5% hydrochloric acid
  6. washthe solution was washed with ethyl acetate
  7. customThe aqueous layer was separated
  8. filtrationThe resulting precipitate was filtered
  9. customrecrystallized from a mixture of ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-9be1b5f44fce465aa15c1c5b83fdef0e
Source dataset
uspto-grants-1984_04
Patent number
US04443607

Reaction notes

Loading…