5-Methyl-3-nitropyridin-2-amine → 5-Methylpyridine-2,3-diamine

HRID 343781Notes

Reaction equation

HRID 343781 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([CH3:11])=[CH:4][N:3]=1>[Pd].CO>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([CH3:11])=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 3456445-Methyl-3-nitropyridin-2-amine

Product 1

HCID 107018255-Methylpyridine-2,3-diamineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 38 (790 mg, 5.17 mmol), methanol (60 mL), and 5% Pd-C (70 mg) was shaken under H2 (20-30 psi) for 3 h, then filtered and evaporated to give 629 mg (99%) of the diamine 39 as a black thick oil. 1H NMR (CDCl3) δ 2.160 (s, 3H), 3.308 (bs, 2H), 4.160 (bs, 2H), 6.740 (s, 1H), 7.459 (s, 1H). It was used for the next reaction without further purification.

Workup

  1. filtrationfiltered
  2. customevaporated

Sources & evidence

ORD record
ord-974b60894ce6487c8835840641438c5b
Source dataset
uspto-grants-1999_01
Patent number
US05863916

Reaction notes

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