Hydrochloric Acid → HCID 9813139, compound

HRID 1740951Notes

Reaction equation

HRID 1740951 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]#[N:10])=[CH:4][N:3]=1.[ClH:11]>C(O)C.CO.[Pd]>[ClH:11].[ClH:11].[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH2:9][NH2:10])=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 99641036-Amino-4-methylnicotinonitrile

Product 1

HCID 9813139HCID 9813139, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of 2-amino-5-cyano-4-methylpyridine (200 mg, 1.50 mmol) in a mixture of ethanol (17 mL) and methanol (7 mL) was hydrogenated for 48 h at atmospheric pressure in the presence of 1N hydrochloric acid (3 mL) and 10% palladium-on-charcoal (50 mg). The catalyst was removed by filtration through Celite, the filter washed with methanol, and the combined filtrate and washings evaporated. Crystallization from chloroform-methanol afforded pure title compound; yield 98 mg (31%).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. washthe filter washed with methanol
  3. customthe combined filtrate and washings evaporated
  4. customCrystallization from chloroform-methanol afforded pure title compound

Sources & evidence

ORD record
ord-e54d9ce8869c4011870f3478086c1da4
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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