2-(6-Methyl-5-nitro-pyridin-2-ylsulfanyl)-ethanol → 2-(5-Amino-6-methyl-pyridin-2-ylsulfanyl)-ethanol

HRID 1811560Notes

Reaction equation

HRID 1811560 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][CH2:10][OH:11])[CH:5]=[CH:4][C:3]=1[N+:12]([O-])=O>[Zn].C(O)(=O)C>[NH2:12][C:3]1[CH:4]=[CH:5][C:6]([S:8][CH2:9][CH2:10][OH:11])=[N:7][C:2]=1[CH3:1]

Participants

4

Reactant 1

HCID 114244292-(6-Methyl-5-nitro-pyridin-2-ylsulfanyl)-ethanol

Product 1

HCID 685686312-(5-Amino-6-methyl-pyridin-2-ylsulfanyl)-ethanolYield 33.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a suspension of 2-(6-methyl-5-nitro-pyridin-2-ylsulfanyl)-ethanol (323 mg, 1.5 mmol) and 7 ml of acetic acid, zinc dust (220 mg, 3.4 mmol) was added at 0° C. The mixture was stirred at room temperature for 2 hr. Zinc dust was filtered through celite and the residue was purified by HPLC to provide 2-(5-amino-6-methyl-pyridin-2-ylsulfanyl)-ethanol as an oil (93 mg, 33%). 1HNMR (DMSO-d4, 400 MHz) δ 1.91 (s, 1H), 2.38 (s, 3H), 2.50-2.51 (m, 2H), 3.12-3.15 (m, 2H), 3.57-3.61 (m, 2H), 7.26-7.28 (m, 1H), 734-7.36 (m, 1H). Exact mass calculated for C8H12N2OS 184.07 found 184.9 (MH+).

Workup

  1. additionwas added at 0° C
  2. filtrationZinc dust was filtered through celite
  3. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-8d8df57d01624d1c887938c4fcf23491
Source dataset
uspto-grants-2013_01
Patent number
US08362248B2

Reaction notes

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