Methanol → 4-Cyclopropylpyridin-3-amine

HRID 1844034Notes

Reaction equation

HRID 1844034 reaction equation
[Cl-].[NH4+].[CH:3]1([C:6]2[CH:11]=[CH:10][N:9]=[CH:8][C:7]=2[N+:12]([O-])=O)[CH2:5][CH2:4]1.CO>C1COCC1.C(Cl)(Cl)Cl.[Zn]>[CH:3]1([C:6]2[CH:11]=[CH:10][N:9]=[CH:8][C:7]=2[NH2:12])[CH2:5][CH2:4]1

Participants

7

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 668018544-Cyclopropyl-3-nitropyridine

Product 1

HCID 668019694-Cyclopropylpyridin-3-amineYield 787.3%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

Zinc powder (223.2 mg, 3.41 mmol) and ammonium chloride solution (365 mg, 6.8 mmol) were added to a stirred solution of 4-cyclopropyl-3-nitropyridine (70 mg, 0.426 mmol) in dry THF (2 mL) at 0° C. and the resulting mixture was stirred at room temperature for 1 hour. The reaction was monitored by TLC (10% methanol in CHCl3). The organic layer was concentrated and washed with pentane to afford 450 mg of the product (100% yield).

Workup

  1. concentrationThe organic layer was concentrated
  2. washwashed with pentane

Sources & evidence

ORD record
ord-05a9a7d74b5040ec97a2758b1b7038b9
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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