2-Chloro-3-methyl-5-nitropyridine → 6-Chloro-5-methylpyridin-3-amine

HRID 930484Notes

Reaction equation

HRID 930484 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1>C(O)(=O)C.O.[Fe]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([NH2:9])=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 1

HCID 896482-Chloro-3-methyl-5-nitropyridine

Product 1

HCID 122956076-Chloro-5-methylpyridin-3-amine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 21899381Acetic acid--water (1/1)Solvent

Procedure

Fe powder (9.75 g, 0.174 mol, Sigma-Aldrich) was added in portions over a period of 2 h to a stirred solution of 2-chloro-3-methyl-5-nitropyridine (10 g, 0.058 mol, Combi-blocks) in acetic acid/water (29 mL: 88 mL). After 3 h, the reaction mixture was filtered through celite and the filter cake was washed with ethyl acetate. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with aqueous sodium bicarbonate, brine and dried over Na2SO4. The solvent was removed under reduced pressure to yield 6-chloro-5-methylpyridine-3-amine as a brown solid (8.0 g; 97%). MS m/z=142.03 [M+H]+.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. washthe filter cake was washed with ethyl acetate
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were washed with aqueous sodium bicarbonate, brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-665d700fb3f647f695f2ed4210ccbce5
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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