Methanol → 6-Cyclopropyl-4-methoxypyridin-3-amine

HRID 715552Notes

Reaction equation

HRID 715552 reaction equation
[CH:1]1([C:4]2[CH:9]=[C:8]([O:10][CH3:11])[C:7]([N+:12]([O-])=O)=[CH:6][N:5]=2)[CH2:3][CH2:2]1.CO.[BH4-].[Na+]>C(Cl)Cl.C(=O)(O)[O-].[Na+].O.[Ni](Cl)Cl>[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([NH2:12])=[C:8]([O:10][CH3:11])[CH:9]=2)[CH2:3][CH2:2]1

Participants

8

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 867175992-Cyclopropyl-4-methoxy-5-nitropyridine

Product 1

HCID 867176006-Cyclopropyl-4-methoxypyridin-3-amineYield 65.7%

Reagents, catalysts & solvents 4

HCID 24385Nickel DichlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2-cyclopropyl-4-methoxy-5-nitropyridine (805 mg, 4.15 mmol), nickel(II) chloride, 6H2O (2956 mg, 12.44 mmol), and methanol (25 mL), cooled to 0° C., was added sodium borohydride (941 mg, 24.87 mmol) portion wise over 1 minute. After 5 minutes, the reaction was diluted with DCM (50 mL), saturated sodium bicarbonate (50 mL), and water (50 mL), and filtered through Celite©. The layers of the filtrate were separated and the aqueous layer was further extracted with DCM (50 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL), eluted through a phase separator, and concentrated to afford 6-cyclopropyl-4-methoxypyridin-3-amine (448 mg, 63%) as a yellow oil. MS (m/z) 165.1 (M+H+).

Workup

  1. filtrationfiltered through Celite©
  2. customThe layers of the filtrate were separated
  3. extractionthe aqueous layer was further extracted with DCM (50 mL)
  4. washThe combined organic extracts were washed with water (50 mL), brine (50 mL)
  5. washeluted through a phase separator
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cce4f66caf86491a8fbf212aa511f68e
Source dataset
uspto-grants-2015_11
Patent number
US09187464B2

Reaction notes

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