Hydrochloric Acid → 6-Cyclopropyl-4-methylpyridin-3-amine

HRID 1527301Notes

Reaction equation

HRID 1527301 reaction equation
[CH:1]1([C:4]2[CH:9]=[C:8]([CH3:10])[C:7]([N+:11]([O-])=O)=[CH:6][N:5]=2)[CH2:3][CH2:2]1.Cl.C([O-])(O)=O.[Na+]>CO.[Zn]>[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([NH2:11])=[C:8]([CH3:10])[CH:9]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 682836712-Cyclopropyl-4-methyl-5-nitropyridine

Product 1

HCID 682833106-Cyclopropyl-4-methylpyridin-3-amine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-cyclopropyl-4-methyl-5-nitropyridine (201 mg, 0.96 mmol) in MeOH (5 mL) were added 3N aqueous HCl (9.6 mL, 28.8 mmol) and Zn powder (376 mg, 5.75 mmol). The mixture was stirred 18 h at RT. The solution was neutralized with a sat. aq. NaHCO3 solution and extracted with CH2Cl2 (3×). The combined organics were dried (Phase Separator) and concentrated under reduced pressure. MS (LC-MS): 149 [M+H]+, tR (HPLC conditions c): 2.22 min.

Workup

  1. extractionextracted with CH2Cl2 (3×)
  2. customThe combined organics were dried (Phase Separator)
  3. concentrationconcentrated under reduced pressure
  4. custom2.22 min.

Sources & evidence

ORD record
ord-26031d8e8de14dcbb3a97d7b2271ad19
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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