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

HRID 1995826Notes

Reaction equation

HRID 1995826 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:22]=[CH:21][C:7]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([NH:16]C(=O)OC)=[N:14][CH:15]=2)=[CH:6][CH:5]=1.CO>O>[NH2:16][C:13]1[CH:12]=[CH:11][C:10]([O:9][CH2:8][C:7]2[CH:21]=[CH:22][C:4]([Cl:3])=[CH:5][CH:6]=2)=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 887Methanol3×HCID 14798Sodium HydroxideHCID 20486108Methyl {5-[(4-chlorophenyl)methoxy]pyridin-2-yl}carbamate

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10% Sodium hydroxide (8 ml) is added to methyl N-[5-(4-chlorobenzyloxy)-2-pyridyl]carbamate (59 mg, 0.20 mmol), and the mixture is heated rapidly to 85°. About 4 ml of methanol is added to the mixture after it has been heated for 2 hours. Heating is continued, and after another hour about 4 ml more of methanol is added to the mixture. Heating at 85° is continued overnight. The reaction is then cooled, and the methanol is rotoevaporated off. The reaction is poured into water and extracted with chloroform. The organic phase is washed with water and with brine to yield 2-amino-5-(4-chlorobenzyloxy)pyridine.

Workup

  1. temperaturethe mixture is heated rapidly to 85°
  2. temperaturehas been heated for 2 hours
  3. temperatureHeating
  4. temperatureHeating at 85°
  5. temperatureThe reaction is then cooled
  6. extractionextracted with chloroform
  7. washThe organic phase is washed with water and with brine

Sources & evidence

ORD record
ord-cf8c0b4eb4464667bb379a1e0f33a78e
Source dataset
uspto-grants-1983_09
Patent number
US04406690

Reaction notes

Loading…