Acetone → 6-(2-Chlorobenzoyl)-5-(2-nitroethenylamino)indan

HRID 258036Notes

Reaction equation

HRID 258036 reaction equation
O1[CH2:6][CH2:5][N:4]([CH:7]=[CH:8][N+:9]([O-:11])=[O:10])CC1.NC1C=[C:15]2[C:19](=[CH:20][C:21]=1[C:22](=[O:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:29])[CH2:18][CH2:17][CH2:16]2.Cl.CC(C)=O>O>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:22]([C:21]1[CH:20]=[C:19]2[C:18]([CH2:17][CH2:16][CH2:15]2)=[CH:6][C:5]=1[NH:4][CH:7]=[CH:8][N+:9]([O-:11])=[O:10])=[O:30]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 683970Morpholine, 4-(2-nitroethenyl)-HCID 199365705-Amino-6-(2-chlorobenzoyl)indan

Product 1

HCID 677827716-(2-Chlorobenzoyl)-5-(2-nitroethenylamino)indanYield 95.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Morpholino-2-nitroethene (3.93 g) was added to a mixture of 5-amino-6-(2-chlorobenzoyl)indan (4.50 g), 6N HCl (15 ml) and acetone (45 ml) and the whole mixture was stirred at room temperature for one hour. To this reaction mixture was added water to give crystals of 6-(2-chlorobenzoyl)-5-(2-nitroethenylamino)indan (5.40 g, 95.2%). Recrystallization from ethanol gave yellow needles, mp. 225°-226° C.

Sources & evidence

ORD record
ord-abb5a35b811545fb94ed193b1144da2e
Source dataset
uspto-grants-1993_11
Patent number
US05264454

Reaction notes

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