Hydrazine hydrate (1:1) → HCID 178482201, compound

HRID 1501269Notes

Reaction equation

HRID 1501269 reaction equation
[OH:1][C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[C:6]([NH: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[NH:11][CH3:12]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178482200HCID 178482200, compound

Product 1

HCID 178482201HCID 178482201, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

2-hydroxy-6-methyl-4-(methylamino)nicotinonitrile (163 mg, 1.0 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 celite, 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)-6-methyl-4-(methylamino)pyridin-2-ol (60 mg, 36% yield) as a brown solid.

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 silica gel column chromatography with dichloromethane/methanol=10:1

Sources & evidence

ORD record
ord-9b948c0197884fa7857b71ff3027a7ac
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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