Nitroethane → 1-(7-Chloro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-9-yl)-2-nitro-1-propene

HRID 2303951Notes

Reaction equation

HRID 2303951 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH2:13][C:6]3=[C:5]([CH:14]=O)[C:4]=2[CH:3]=1.C([O-])(=O)C.[NH4+].[N+:21]([CH2:24][CH3:25])([O-:23])=[O:22]>CO>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH2:13][C:6]3=[C:5]([CH:14]=[C:24]([N+:21]([O-:23])=[O:22])[CH3:25])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 517165Ammonium AcetateHCID 184620977-Chloro-2,3-dihydro-1H-pyrrolo[1,2-a]indole-9-carboxaldehyde

Product 1

HCID 698492581-(7-Chloro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-9-yl)-2-nitro-1-propeneYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 7-chloro-2,3-dihydro-1H-pyrrolo[1,2-a]indole-9-carboxaldehyde (1.0 g, 4.6 mmol) and ammonium acetate (0.4 g, 5.2 mmol) in nitroethane (10 mL) was heated to 100° C. for 1 h, cooled to room temperature, diluted with methanol (30 mL), cooled to 0° C., and filtered. The filter-cake was recrystallised (toluene) to give the product as yellow needles (0.58 g, 46%): mp 162-1623° C.; Found: C, 60.68; H, 4.67; N, 9.98%. C14H13ClN2O2 requires: C, 60.77; H, 4.73; N, 10.12%.

Workup

  1. temperaturecooled to 0° C.
  2. filtrationfiltered
  3. customThe filter-cake was recrystallised (toluene)

Sources & evidence

ORD record
ord-6ea6b4194b9b4ce4a973b4dd09175a34
Source dataset
uspto-grants-2002_08
Patent number
US06433175B1

Reaction notes

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