Hydrochloric Acid → 1-(indan-1-yl)-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

HRID 730415Notes

Reaction equation

HRID 730415 reaction equation
[NH2:1][C:2]1[N:3]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)[CH:4]=[C:5]([C:7]#[N:8])[CH:6]=1.[C:18]([CH2:21][C:22](=O)[CH3:23])(=O)[CH3:19].Cl>C(O)C>[CH:9]1([N:3]2[C:2]3=[N:1][C:18]([CH3:19])=[CH:21][C:22]([CH3:23])=[C:6]3[C:5]([C:7]#[N:8])=[CH:4]2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31261AcetylacetoneHCID 230746595-Amino-1-(2,3-dihydro-1H-inden-1-yl)-1H-pyrrole-3-carbonitrile

Product 1

HCID 230746201-(indan-1-yl)-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrileYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-amino-1-(indan-1-yl)pyrrole-4-carbonitrile (19.4 g), acetylacetone (9.6 g) and ethanol (375 ml) was added concentrated hydrochloric acid (3 ml), and the mixture was heated under reflux for 3 hours. The reaction solution was concentrated under reduced pressure and an aqueous sodium hydrogen carbonate solution was added to the residue, which was 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 crystal was collected by filtration to give 1-(indan-1-yl)-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (11.4 g, 46%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionan aqueous sodium hydrogen carbonate solution was added to the residue, which
  5. extractionwas extracted with ethyl acetate
  6. washAfter the organic layer was washed with water
  7. dry with materialdried (MgSO4)
  8. distillationthe solvent was distilled off under reduced pressure
  9. filtrationthe crystal was collected by filtration

Sources & evidence

ORD record
ord-9e6c8045d888419c817e892eeeea49fd
Source dataset
uspto-grants-2009_09
Patent number
US07582651B2

Reaction notes

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