5-[(4-Chlorophenyl)methoxy]-2-nitropyridine → 5-[(4-Chlorophenyl)methoxy]pyridin-2-amine

HRID 1995839Notes

Reaction equation

HRID 1995839 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]([N+:14]([O-])=O)=[N:12][CH:13]=2)=[CH:4][CH:3]=1>O.CO>[NH2:14][C:11]1[CH:10]=[CH:9][C:8]([O:7][CH2:6][C:5]2[CH:17]=[CH:18][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:13][N:12]=1

Participants

4

Reactant 1

HCID 204861295-[(4-Chlorophenyl)methoxy]-2-nitropyridine

Product 1

HCID 204861125-[(4-Chlorophenyl)methoxy]pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 5-(4-chlorobenzyloxy)-2-nitropyridine (0.5 g), Na2S (0.25 g) and methanol (12 ml) is heated to reflux for about 3 hours. Then, a few drops of water is added and refluxing continued about 15 hours. After cooling, the reaction is diluted with methanol, filtered through celite and stripped. The concentrate is taken up in CHCl3, washed with water, dried and stripped giving 2-amino-5-(4-chlorobenzyloxy)pyridine.

Workup

  1. temperatureis heated
  2. temperatureto reflux for about 3 hours
  3. temperaturerefluxing
  4. temperatureAfter cooling
  5. filtrationfiltered through celite
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-d0b88793ae6c414990b04c5246241a74
Source dataset
uspto-grants-1983_09
Patent number
US04406689

Reaction notes

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