Hydrochloric Acid → 3-Pyridinol, 4-(aminomethyl)-6-(1,1-dimethylethyl)-, hydrochloride (1:2)

HRID 1112720Notes

Reaction equation

HRID 1112720 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[N:6]=[CH:5][C:4]=1[OH:13])#[N:2].[ClH:14]>CO.[Pd]>[ClH:14].[ClH:14].[NH2:2][CH2:1][C:3]1[CH:8]=[C:7]([C:9]([CH3:11])([CH3:10])[CH3:12])[N:6]=[CH:5][C:4]=1[OH:13]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 126342602-(1,1-Dimethylethyl)-5-hydroxy-4-pyridinecarbonitrile

Product 1

HCID 126342623-Pyridinol, 4-(aminomethyl)-6-(1,1-dimethylethyl)-, hydrochloride (1:2)

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-cyano-6-(1,1-dimethylethyl)-3-pyridinol (5.7 g., 0.032 mole) in methanol -- 12N hydrochloric acid (30:1; v:v; 310 ml.) is hydrogenated in the presence of 10% palladium on charcoal (1 g.) in a Parr apparatus at 25° C. and 40-45 p.s.i. pressure until the theoretical quantity of hydrogen has been consumed. Then the hydrogenation mixture is filtered and the collected catalyst, washed with ethanol. Evaporation (in vacuo) of the combined filtrate and washings leaves the 4-aminomethyl-6-(1,1-dimethylethyl)-3-pyridinol dihydrochloride as a residual solid (7.9 g., 98%), m.p. 304°-306° C. with dec. Recrystallization of the solid from ethanol-ether-water (100:100:4; v:v:v) affords an analytical sample of 4-aminomethyl-6-(1,1-dimethylethyl)-3-pyridinol dihydrochloride as colorless crystals, m.p. 304°-306° C. with dec.

Workup

  1. custompressure until the theoretical quantity of hydrogen has been consumed
  2. filtrationThen the hydrogenation mixture is filtered
  3. washthe collected catalyst, washed with ethanol
  4. customEvaporation (in vacuo) of the combined filtrate and washings

Sources & evidence

ORD record
ord-215c1bcd324e4b4fb2acf26cf37ae888
Source dataset
uspto-grants-1978_10
Patent number
US04123537

Reaction notes

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