Hydrazine hydrate (1:1) → HCID 178428522, compound
Reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([OH:10])[N:5]=[C:4]([CH3:11])[CH:3]=1.O.NN>C(O)C.[Ni]>[NH2:1][C:2]1[CH:3]=[C:4]([CH3:11])[N:5]=[C:6]([OH:10])[C:7]=1[CH2:8][NH2:9]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
4-amino-2-hydroxy-6-methylnicotinonitrile (350 mg, 2.4 mmol) was dissolved in ethanol (15 mL) and warmed to 50° C. before it was treated with raney nickel (1 ml slurry in water) followed by addition of hydrazine monohydrate (2 ml). The resulting mixture was allowed to stir at 50° 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 4-amino-3-(aminomethyl)-6-methylpyridin-2-ol (200 mg, 56% yield) as a yellow solid.
Workup
- customThe cooled reaction mixture
- filtrationwas filtered through celite
- washrinsed with methanol
- concentrationThe filtrate was concentrated in vacuo
- customto provide crude product which
- customwas purified by silica gel column chromatography with dichloromethane/methanol=10:1
Sources & evidence
- ORD record
- ord-20c8c35a76374db69d65e99adbe36d79
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206128B2
Reaction notes
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