HCID 13713867, compound → HCID 178516726, compound

HRID 651916Notes

Reaction equation

HRID 651916 reaction equation
C[O:2][C:3]([CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:21](=[O:22])[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[C:14]2=[O:23])=[CH:9][C:8]=1[N+:24]([O-])=O)=O>C(O)(=O)C.C(OCC)(=O)C.O.[Fe]>[NH:24]1[C:8]2[C:7](=[CH:12][CH:11]=[C:10]([N:13]3[C:14](=[O:23])[C:15]4[CH2:16][CH2:17][CH2:18][CH2:19][C:20]=4[C:21]3=[O:22])[CH:9]=2)[NH:6][CH2:5][C:3]1=[O:2]

Participants

6

Reactant 1

HCID 13713867HCID 13713867, compound

Product 1

HCID 178516726HCID 178516726, compoundYield 76.3%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Methoxycarbonylmethylamino-3-nitrophenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (2.06 g) was dissolved in a mixture of acetic acid (20 ml) and ethyl acetate (20 ml), and the resultant solution was dropwise added to a mixture of 5% aqueous acetic acid (10 ml) and iron powder (4 g) at 70° to 80° C., followed by stirring at the same temperature for 3 hours. The reaction mixture was allowed to cool, diluted with water and extracted with ethyl acetate. The extract was washed with sodium bicarbonate solution, dried and concentrated to give 2-(3,4-dihydro-2(1H)-quinoxalinon-7-yl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (1.3 g). m.p., 208°-209° C.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with sodium bicarbonate solution
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-94f6b1a25d904b88a1f2413561719762
Source dataset
uspto-grants-1987_06
Patent number
US04670042

Reaction notes

Loading…