4-Amino-5-chloro-2-methoxybenzoic acid → HCID 14881838, compound

HRID 1608189Notes

Reaction equation

HRID 1608189 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH:5]1[O:10][CH2:9][CH2:8][N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1.[NH2:18][C:19]1[C:27]([Cl:28])=[CH:26][C:22]([C:23](O)=[O:24])=[C:21]([O:29][CH3:30])[CH:20]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[NH2:18][C:19]1[C:27]([Cl:28])=[CH:26][C:22]([C:23]([NH:1][CH2:2][CH2:3][CH2:4][CH:5]2[O:10][CH2:9][CH2:8][N:7]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:6]2)=[O:24])=[C:21]([O:29][CH3:30])[CH:20]=1

Participants

5

Reactant 3

HCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14881837HCID 14881837, compound

Product 1

HCID 14881838HCID 14881838, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of 2-(3-aminopropyl)-4-benzylmorpholine (2.0 g), 4-amino-5-chloro-2-methoxybenzoic acid (1.7 g) and dichloromethane (40 ml), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.8 g) is added, and the mixture is stirred at 25° C. for 4 hours. The reaction mixture is washed successively with water, 10% aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and evaporated 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 (2.5 g) as an oil.

Workup

  1. additionis added
  2. washThe reaction mixture is washed successively with water, 10% aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. dissolutionThe residue is dissolved in chloroform
  6. customchromatographed on silica gel
  7. customevaporated

Sources & evidence

ORD record
ord-770e1f5201c1465dbc1d1bfe0757698e
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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