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

HRID 326022Notes

Reaction equation

HRID 326022 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[NH2:9][CH:10]([CH3:29])[CH2:11][N:12]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:28]>C(OCC)(=O)C>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[NH2:9][CH:10]([CH3:29])[CH2:11][N:12]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:28]

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 132699402-(2-aminopropyl)-4-phenyl-1(2H)-isoquinolone

Product 1

HCID 132699412-(2-aminopropyl)-4-phenyl-1(2H)-isoquinolone maleateYield 83.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

6 g of maleic acid was added to 14 g of 2-(2-aminopropyl)-4-phenyl-1(2H)-isoquinolone prepared as described above in 80 ml of ethyl acetate, and the mixture was stirred while warming. The crystals precipitated upon cooling were collected by filtration and recrystallized from a mixture of ethanol and ethyl acetate to obtain 16.5 g of 2-(2-aminopropyl)-4-phenyl-1(2H)-isoquinolone maleate having a melting point of 187° C. as colorless prisms.

Workup

  1. customprepared
  2. temperaturewhile warming
  3. customThe crystals precipitated
  4. temperatureupon cooling
  5. filtrationwere collected by filtration
  6. customrecrystallized from a mixture of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-081964e6d3af417da675f502f7bf58bd
Source dataset
uspto-grants-1984_04
Patent number
US04443607

Reaction notes

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