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

HRID 53595Notes

Reaction equation

HRID 53595 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) δ2.160 (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-532db622620a4108a387e0243ffee529
Source dataset
uspto-grants-1997_04
Patent number
US05620978

Reaction notes

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