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4-Amino-5-chloro-2-methoxybenzoic acid → 4-amino-5-chloro-N-[(4-ethoxycarbonyl-2-morpholinyl)methyl]-2-methoxybenzamide

HRID 1608190
Notes
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Reaction equation

HRID 1608190 reaction equation
[NH2:1][CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4]1.[NH2:14][C:15]1[C:23]([Cl:24])=[CH:22][C:18]([C:19](O)=[O:20])=[C:17]([O:25][CH3:26])[CH:16]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[NH2:14][C:15]1[C:23]([Cl:24])=[CH:22][C:18]([C:19]([NH:1][CH2:2][CH:3]2[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4]2)=[O:20])=[C:17]([O:25][CH3:26])[CH:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14877395Ethyl 2-(aminomethyl)morpholine-4-carboxylate

Product 1

HCID 148773964-amino-5-chloro-N-[(4-ethoxycarbonyl-2-morpholinyl)methyl]-2-methoxybenzamideYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2-aminomethyl-4-ethoxycarbonylmorpholine (5.8 g) in dichloromethane (100 ml), 4-amino-5-chloro-2-methoxybenzoic acid (5.0 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.2 g) are added, and the resulting mixture is stirred at 25° C. for 4 hours. The reaction mixture is washed successively with water, aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, and dried over magnesium sulfate. The solvent is distilled off under reduced pressure. The residue is dissolved in chloroform and chromatographed on silica gel. The eluate with chloroform is discarded, and the subsequent eluates with methanol-chloroform (1:9) are pooled and evaporated to give the title compound (7.5 g) as an oil.

Workup

  1. washThe reaction mixture is washed successively with water, aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. distillationThe solvent is distilled off under reduced pressure
  4. dissolutionThe residue is dissolved in chloroform
  5. customchromatographed on silica gel
  6. customevaporated

Sources & evidence

ORD record
ord-50147ce3283a4e3f91f06ffb648bcc5a
Source dataset
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04870074

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes