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

HRID 1501219Notes

Reaction equation

HRID 1501219 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
55 °C

Procedure

2-hydroxy-4-methoxy-6-methylnicotinonitrile (70 mg, 0.43 mmol) was dissolved in ethanol (10 mL) and was warmed to 55° C. before it was treated with Raney nickel (0.5 mL slurry in water) followed by addition of hydrazine monohydrate (2 mL). The resulting mixture was allowed to stir at 55° C. for 2 hours. The cooled reaction mixture was filtered through diatomaceous earth, rinsed with methanol. The filtrate was concentrated in vacuo to provide crude product which was purified by silica gel column chromatography with dichloromethane/methanol=10:1 to afford 3-(aminomethyl)-4-methoxy-6-methylpyridin-2-ol (40 mg, 56% yield) as a yellow solid. 1H NMR (300 MHz, DMSO-d6): δ 6.04 (s, 1H), 4.87 (br s, 3H), 3.77 (s, 3H), 3.42 (s, 2H), 2.15 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-5eed4de1b2fc4d10b91ef05a1b8fcd82
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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