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

HRID 36929Notes

Reaction equation

HRID 36929 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-223d5f6f070c4357b70dc067fd0a20e8
Source dataset
uspto-grants-1995_05
Patent number
US05418239

Reaction notes

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