Hydrazine hydrate (1:1) → HCID 178492315, compound

HRID 1500969Notes

Reaction equation

HRID 1500969 reaction equation
[OH:1][C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[C:6]([O:11][CH3:12])[C:3]=1[C:4]#[N:5].O.NN>C(O)C.[Ni]>[NH2:5][CH2:4][C:3]1[C:2]([OH:1])=[N:9][C:8]([CH3:10])=[CH:7][C:6]=1[O:11][CH3:12]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178492314HCID 178492314, compound

Product 1

HCID 178492315HCID 178492315, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

2-Hydroxy-4-methoxy-6-methylnicotinonitrile (70 mg, 0.43 mmol) was dissolved in ethanol (10 mL) and warmed to 60° C. before it was treated with raney nickel (0.5 mL slurry in water) followed by addition of hydrazine monohydrate (2 mL). The resultant mixture was allowed to stir at 60° C. for 2 hours. The cooled reaction mixture was filtered through celite and rinsed with methanol. The filtrate was concentrated in vacuo to provide crude product which was purified by column chromatography (silica gel, dichloromethane/methanol=10:1) to afford 3-(aminomethyl)-4-methoxy-6-methylpyridin-2-ol (40 mg, 56%) as a white solid. LRMS (M+H+) m/z: calcd 168.09. found 168. HPLC purity (214 nm): 73%. 1H NMR (300 MHz, d6-DMSO): δ 6.04 (s, 1H), 3.77 (s, 3H), 3.42 (s, 2H), 2.15 (s, 3H).

Workup

  1. customThe cooled reaction mixture
  2. filtrationwas filtered through celite
  3. washrinsed with methanol
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto provide crude product which
  6. customwas purified by column chromatography (silica gel, dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-da71d0fb669f4b548147fd8173489f3f
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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