Hydrochloric Acid → 2-Amino-3-(2,6-dimethylbenzyloxy)-5-methylpyridine

HRID 1386095Notes

Reaction equation

HRID 1386095 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([N+:13]([O-])=O)=[N:8][CH:9]=[C:10]([CH3:12])[CH:11]=1.Cl.O>[Fe].C(O)C>[NH2:13][C:7]1[C:6]([O:5][CH2:4][C:3]2[C:16]([CH3:20])=[CH:17][CH:18]=[CH:19][C:2]=2[CH3:1])=[CH:11][C:10]([CH3:12])=[CH:9][N:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 217173323-(2,6-Dimethylbenzyloxy)-5-methyl-2-nitropyridine

Product 1

HCID 217173172-Amino-3-(2,6-dimethylbenzyloxy)-5-methylpyridineYield 92.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(2,6-dimethylbenzyloxy)-5-methyl-2-nitropyridine (1.9 g, 6.99 mmol), iron powder (6.4 g), concentrated HCl (0.15 ml), water (1.5 ml) and 95% ethanol (35 ml) was refluxed for 1.0 h. The reaction mixture was filtered over celite and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel, using methylene chloride:methanol (100:4) as eluent to give 1.56 g (92%) of the title compound.

Workup

  1. temperaturewas refluxed for 1.0 h
  2. filtrationThe reaction mixture was filtered over celite
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-621e55e1723c405e9bb8a6086c68e702
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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