N-(4-Nitrophenyl)pyridin-2-amine → N-pyridin-2-yl-benzene-1,4-diamine

HRID 450065Notes

Reaction equation

HRID 450065 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:6][CH:5]=1)([O-])=O>C(OCC)(=O)C>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[NH:10][C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 12695755N-(4-Nitrophenyl)pyridin-2-amine

Product 1

HCID 10375156N-pyridin-2-yl-benzene-1,4-diamineYield 33.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (4-nitro-phenyl)-pyridin-2-yl-amine (280 mg, 1.3 mmol) in ethyl acetate (10 ml) was added stannous chloride dihydrate (1.17 g, 5.2 mmol) and stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate and washed with 10% sodium hydroxide solution. The organic layer was separated, washed with brine, dried and evaporated to dryness. Purification by column chromatography using ethyl acetate/hexane (2:3) yielded N-pyridin-2-yl-benzene-1,4-diamine (80 mg, 33%).

Workup

  1. washwashed with 10% sodium hydroxide solution
  2. customThe organic layer was separated
  3. washwashed with brine
  4. customdried
  5. customevaporated to dryness
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-20b74450bf6e4cebb4f88ac854b99de8
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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