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

HRID 1995830Notes

Reaction equation

HRID 1995830 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 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 (4×). 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 (4×)
  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-5ac3df67d5784485bc35c3abede7217d
Source dataset
uspto-grants-1983_09
Patent number
US04406690

Reaction notes

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