Methanol → 4-Cyclopropylpyridin-3-amine

HRID 572369Notes

Reaction equation

HRID 572369 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 (I-1a: 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 reaction mixture was filtered over celite bed and washed with THF and filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with water and saturated brine and dried over sodium sulphate and concentrated to afford 450 mg of the product (100% yield).

Workup

  1. filtrationThe reaction mixture was filtered over celite bed
  2. washwashed with THF and filtrate
  3. concentrationwas concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water and saturated brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-efe3770be40548cdb07366c69f568db4
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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