Potassium Hydroxide → Benzamide, 4-amino-5-chloro-2-methoxy-N-(2-morpholinylmethyl)-

HRID 1608196Notes

Reaction equation

HRID 1608196 reaction equation
[NH2:1][C:2]1[C:22]([Cl:23])=[CH:21][C:5]([C:6]([NH:8][CH2:9][CH:10]2[O:15][CH2:14][CH2:13][N:12](C(OCC)=O)[CH2:11]2)=[O:7])=[C:4]([O:24][CH3:25])[CH:3]=1.[OH-].[K+]>C(O)(C)C>[NH2:1][C:2]1[C:22]([Cl:23])=[CH:21][C:5]([C:6]([NH:8][CH2:9][CH:10]2[O:15][CH2:14][CH2:13][NH:12][CH2:11]2)=[O:7])=[C:4]([O:24][CH3:25])[CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 148773964-amino-5-chloro-N-[(4-ethoxycarbonyl-2-morpholinyl)methyl]-2-methoxybenzamide

Product 1

HCID 10859540Benzamide, 4-amino-5-chloro-2-methoxy-N-(2-morpholinylmethyl)-Yield 28.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-amino-5-chloro-N-[(4-ethoxycarbonyl-2-morpholinyl)methyl]-2-methoxybenzamide (6.1 g), potassium hydroxide (10.1 g), and isopropyl alcohol (60 ml) is refluxed with stirring for 3 hours. The reaction mixture is concentrated under reduced pressure, and the residue is diluted with water and extracted with chloroform. The organic layer is washed successively with water and saturated aqueous sodium chloride solution, and dried over magnesium sulfate. The solvent is distilled off under reduced pressure, and the residue is recrystallized from isopropyl alcohol to give the title compound (1.4 g), mp 161°-162° C.

Workup

  1. temperatureis refluxed
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. additionthe residue is diluted with water
  4. extractionextracted with chloroform
  5. washThe organic layer is washed successively with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent is distilled off under reduced pressure
  8. customthe residue is recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-26c5b00e446445b7983ad23a036bf683
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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