Nitroethane → 8-(2-Nitro-propenyl)-2,3-dihydro-1H-3a,6-diaza-cyclopenta[a]indene

HRID 1370182Notes

Reaction equation

HRID 1370182 reaction equation
[CH2:1]1[C:5]2=[C:6]([CH:13]=O)[C:7]3[CH:8]=[N:9][CH:10]=[CH:11][C:12]=3[N:4]2[CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+].[N+:20]([CH2:23][CH3:24])([O-:22])=[O:21]>>[N+:20]([C:23]([CH3:24])=[CH:13][C:6]1[C:7]2[CH:8]=[N:9][CH:10]=[CH:11][C:12]=2[N:4]2[CH2:3][CH2:2][CH2:1][C:5]=12)([O-:22])=[O:21]

Participants

4

Reactant 3

HCID 6587NitroethaneHCID 517165Ammonium AcetateHCID 155163562,3-Dihydro-1H-3a,6-diaza-cyclopenta[a]indene-8-carbaldehyde

Product 1

HCID 696404338-(2-Nitro-propenyl)-2,3-dihydro-1H-3a,6-diaza-cyclopenta[a]indeneYield 77%

Conditions

Temperature
100 °C

Procedure

To a solution of 2,3-dihydro-1H-3a,6-diaza-cyclopenta[a]indene-8-carbaldehyde (0.30 g 1.6 mMol) in nitroethane (3.00 ml) was added ammonium acetate (0.30 g 3.9 mMol) and the mixture was heated to 100° C. for 4 h with stirring under argon. The mixture was cooled to room temperature and purified by chromatography on silicagel gel (ca 30 g) eluting first with ethyl acetate (ca 100 ml) then with a mixture of ethyl acetate (9 parts) and methanol (1 part). The product fraction were combined, concentrated and the residue was recrystallised from ethyl acetate to yield the title compound (0.30 g, 77%) as yellow crystals. mp 141-142° C. Found C, 64.05; H, 5.51; N, 17.14%; C13H13N3O2 requires C, 64.19; H, 5.39; N, 17.27%.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompurified by chromatography on silicagel gel (ca 30 g)
  3. washeluting first with ethyl acetate (ca 100 ml)
  4. additionwith a mixture of ethyl acetate (9 parts) and methanol (1 part)
  5. concentrationconcentrated
  6. customthe residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-64d2ea781a1a4ad992f99ad135a1190a
Source dataset
uspto-grants-2003_06
Patent number
US06583134B2

Reaction notes

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