2-Amino-3-nitro-5-p-tolylpyridine → 2,3-Diamino-5-p-tolyl-pyridine

HRID 2250399Notes

Reaction equation

HRID 2250399 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[CH:4][N:3]=1.[H][H]>CO.[Pd]>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 218827162-Amino-3-nitro-5-p-tolylpyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 218827182,3-Diamino-5-p-tolyl-pyridineYield 93.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3.25 g of 2-amino-5-(p-tolyl)-3-nitro-pyridine (compound G3) and 325 mg of Pd/C (10%) in 260 ml of methanol is treated with hydrogen under vigorous stirring at room temperature for 18 h. The suspension is filtered with suction through a celite pad. The colorless filtrate is evaporated to dryness to afford 2.63 g of the pure title compound of m.p. 141° C. MS: 200.3 (MH+).

Workup

  1. filtrationThe suspension is filtered with suction through a celite pad
  2. customThe colorless filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-dcc5b0bb9e614bc586a0e98b2ee0cee8
Source dataset
uspto-grants-2008_01
Patent number
US07317021B2

Reaction notes

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