Hydrochloric Acid → {1H-pyrrolo[2,3-c]pyridin-5-yl}methanamine dihydrochloride

HRID 398337Notes

Reaction equation

HRID 398337 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH:9]=[CH:10]N(C)C)[C:6]([N+:14]([O-])=O)=[CH:5][N:4]=1)#[N:2].[ClH:17]>[Pd].CO>[ClH:17].[ClH:17].[NH2:2][CH2:1][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][N:4]=1)[NH:14][CH:10]=[CH:9]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54259741HCID 54259741, compound

Product 1

HCID 23000163{1H-pyrrolo[2,3-c]pyridin-5-yl}methanamine dihydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 2-cyano-4-(2-dimethylaminoethenyl)-5-nitropyridine (3.8 g) and 10% palladium on carbon (3 g) in 6 M HCl (10 mL) and methanol (50 mL) was shaken on a Parr apparatus under hydrogen (55 psi). After 16 h the mixture was filtered through celite, washing with methanol, and was basified with ammonium hydroxide and evaporated in vacuo. The crude product was purified by flash column chromatography (80:19:1 chloroform/methanol/ammonium hydroxide) to give the title compound as the free base. The free base was dissolved in a minimum volume of methanol and 1 M HCl in ether (2 equivalents) was added and after dilution with ether the solids were collected by filtration to give the title compound as a tan solid:

Workup

  1. filtrationAfter 16 h the mixture was filtered through celite
  2. washwashing with methanol
  3. customevaporated in vacuo
  4. customThe crude product was purified by flash column chromatography (80:19:1 chloroform/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-ea4ca5f7d7e04485bc5fa5ab3e8c9d88
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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