Ammonium Acetate → 3-Amino-1-(4-chlorophenyl)-1,2-dihydroquinoxalin-2-one

HRID 848479Notes

Reaction equation

HRID 848479 reaction equation
C([O-])(=O)C.[NH4+:5].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15](OCC)[C:14]2=[O:26])=[CH:9][CH:8]=1>O>[NH2:5][C:15]1[C:14](=[O:26])[N:13]([C:10]2[CH:11]=[CH:12][C:7]([Cl:6])=[CH:8][CH:9]=2)[C:22]2[C:17]([N:16]=1)=[CH:18][CH:19]=[CH:20][CH:21]=2

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 205654531-(4-Chlorophenyl)-1,2-dihydro-3-ethoxyquinoxalin-2-one

Product 1

HCID 205654823-Amino-1-(4-chlorophenyl)-1,2-dihydroquinoxalin-2-oneYield 70.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a melt of ammonium acetate (62 g) at 160° C. was added 1-(4-chlorophenyl)-1,2-dihydro-3-ethoxyquinoxalin-2-one (8.8 g) and the temperature was then raised during 5 minutes to 200° C. and maintained at this level for 15 minutes. The melt was cooled, water was added, and the product was filtered off. Crystallisation from ethanol gave the title compound (5.6 g) mp 254°-255° C.

Workup

  1. temperaturethe temperature was then raised during 5 minutes to 200° C.
  2. temperaturemaintained at this level for 15 minutes
  3. temperatureThe melt was cooled
  4. filtrationthe product was filtered off
  5. customCrystallisation from ethanol

Sources & evidence

ORD record
ord-6a044e9c5d98424e8147b462d0d79187
Source dataset
uspto-grants-1981_10
Patent number
US04296114

Reaction notes

Loading…