Acetic Acid → 5-Amino-1-(2,3-dihydro-1H-inden-1-yl)-1H-pyrrole-3-carbonitrile

HRID 730414Notes

Reaction equation

HRID 730414 reaction equation
[K].[CH:2]([CH:4]([CH2:7][C:8]#[N:9])[C:5]#[N:6])=O.[NH2:10][CH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1.C(O)(=O)C.C(=O)([O-])[O-].[K+].[K+]>O>[NH2:9][C:8]1[N:10]([CH:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12]2)[CH:2]=[C:4]([C:5]#[N:6])[CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 123445(+-)-1-AminoindanHCID 86606793HCID 86606793, compound

Product 1

HCID 230746595-Amino-1-(2,3-dihydro-1H-inden-1-yl)-1H-pyrrole-3-carbonitrileYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

Formyl succinonitrile potassium salt (36.5 g) and 1-aminoindane (36.6 g) were dissolved in water (100 ml), and acetic acid (100 ml) was added thereto. After agitating the mixture at 100° C. for 30 minutes, the reaction solution was poured into water (1200 ml). The reaction mixture was made basic by adding potassium carbonate and then extracted with ethyl acetate. After the organic layer was washed with water and dried (MgSO4), the solvent was distilled off under reduced pressure and the residue (37.4 g) was dissolved in ethanol (450 ml). After potassium ethoxide (35.2 g) was added thereto and the mixture was stirred at room temperature for 30 minutes, the reaction solution was poured into iced water (1500 ml) and extracted with ethyl acetate. After the organic layer was washed with water and dried (MgSO4), the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography eluting with ethyl acetate-hexane (1:2, v/v) and the fractions were concentrated under reduced pressure to give 2-amino-1-(indan-1-yl)pyrrole-4-carbonitrile (20.4 g, 37%) as oily matter.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the organic layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off under reduced pressure
  5. dissolutionthe residue (37.4 g) was dissolved in ethanol (450 ml)
  6. additionAfter potassium ethoxide (35.2 g) was added
  7. stirringthe mixture was stirred at room temperature for 30 minutes
  8. additionthe reaction solution was poured into iced water (1500 ml)
  9. extractionextracted with ethyl acetate
  10. washAfter the organic layer was washed with water
  11. dry with materialdried (MgSO4)
  12. distillationthe solvent was distilled off under reduced pressure
  13. washeluting with ethyl acetate-hexane (1:2, v/v)
  14. concentrationthe fractions were concentrated under reduced pressure

Sources & evidence

ORD record
ord-b4474391117e4879995c4d8302fc2488
Source dataset
uspto-grants-2009_09
Patent number
US07582651B2

Reaction notes

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