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

HRID 1608197
Notes
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Reaction equation

HRID 1608197 reaction equation
[NH2:1][C:2]1[C:24]([Cl:25])=[CH:23][C:5]([C:6]([NH:8][CH2:9][CH:10]2[O:15][CH2:14][CH2:13][N:12](CC3C=CC=CC=3)[CH2:11]2)=[O:7])=[C:4]([O:26][CH3:27])[CH:3]=1.C(O)C>[Pd].C(O)(=O)C>[NH2:1][C:2]1[C:24]([Cl:25])=[CH:23][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:26][CH3:27])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 702EthanolHCID 1972374-amino-N-((4-benzyl-2-morpholinyl)methyl)-5-chloro-2-methoxybenzamide

Product 1

HCID 10859540Benzamide, 4-amino-5-chloro-2-methoxy-N-(2-morpholinylmethyl)-Yield 98.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 4-amino-N-[(4-benzyl-2-morpholinyl)methyl]-5-chloro-2-methoxybenzamide (5.0 g), ethanol (100 ml), and acetic acid (20 ml) is hydrogenated over 10% palladium on carbon (0.5 g) at 25° C. After the calculated amount of hydrogen is absorbed, the catalyst is filtered off. The filtrate is evaporated under reduced pressure to give the title compound (3.8 g).

Workup

  1. customAfter the calculated amount of hydrogen is absorbed
  2. filtrationthe catalyst is filtered off
  3. customThe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-64763968cf554ea782572fdab681598b
Source dataset
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04870074

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes