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

HRID 1995848Notes

Reaction equation

HRID 1995848 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]([NH:14]C(=O)OC)=[N:12][CH:13]=2)=[CH:4][CH:3]=1.C(Cl)(Cl)Cl.O>[OH-].[Na+].CO>[NH2:14][C:11]1[CH:10]=[CH:9][C:8]([O:7][CH2:6][C:5]2[CH:19]=[CH:20][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:13][N:12]=1

Participants

6

Reactant 3

HCID 962WaterHCID 6212ChloroformHCID 20486108Methyl {5-[(4-chlorophenyl)methoxy]pyridin-2-yl}carbamate

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 14798Sodium HydroxideSolvent2×

Procedure

A slurry of methyl 5-(4-chlorobenzyloxy)-2-pyridylcarbamate (0.75 g, 2.6 mmol) in 10% sodium hydroxide (20 ml) and methanol (40 ml) is heated to 90° under nitrogen gas. After 1 hour, 10 ml of 10% sodium hydroxide and 10 ml of methanol are added. Heating is continued, and after 2 hours, 10 ml more of methanol is added. The reaction is heated under reflux overnight. The reaction is then rotoevaporated, and chloroform and water are added. The residue is extracted with chloroform (4X). The combined chloroform extracts are washed with water until neutral and with brine, dried over calcium sulfate, filtered and rotoevaporated to yield 2-amino-5-(4-chlorobenzyloxy)pyridine.

Workup

  1. temperatureHeating
  2. waitafter 2 hours
  3. temperatureThe reaction is heated
  4. temperatureunder reflux overnight
  5. extractionThe residue is extracted with chloroform (4X)
  6. washThe combined chloroform extracts are washed with water until neutral and with brine
  7. dry with materialdried over calcium sulfate
  8. filtrationfiltered

Sources & evidence

ORD record
ord-6c41acce402041c6900ca3b6a3d91710
Source dataset
uspto-grants-1983_09
Patent number
US04406689

Reaction notes

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