Pyridine → 2-(3-Chloromethyl-benzoylamino)-5-dipropylamino-benzoic acid methyl ester

HRID 1094983Notes

Reaction equation

HRID 1094983 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])[CH:7]=[CH:6][C:5]=1[NH2:17].N1C=CC=CC=1.CO[C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=1OC)[C:30](Cl)=[O:31].[CH2:38]([Cl:40])Cl>>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])[CH:7]=[CH:6][C:5]=1[NH:17][C:30](=[O:31])[C:29]1[CH:33]=[CH:34][CH:35]=[C:27]([CH2:38][Cl:40])[CH:28]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 77070Veratroyl chloride2×HCID 613136502-Amino-5-dipropylamino-benzoic acid methyl ester2×

Product 1

HCID 666377432-(3-Chloromethyl-benzoylamino)-5-dipropylamino-benzoic acid methyl ester

Conditions

Temperature
0 °C

Procedure

2-Amino-5-dipropylamino-benzoic acid methyl ester (compound A) (243 mg) produced by the above reaction was dissolved in anhydrous methylene chloride (3.0 ml). Subsequently, pyridine (170 μl) and 3-(chloromethyl)benzoyl chloride (compound B) (166 μl) were added to the solution at 0° C., and the mixture was stirred at 0° C. for one hr. After the completion of the reaction, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography using a hexane-acetone system to give 2-(3-chloromethyl-benzoylamino)-5-dipropylamino-benzoic acid methyl ester as a useful intermediate (280 mg, yield 64%).

Workup

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionthe mixture was subjected to separatory extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialwas dried over sodium sulfate
  7. concentrationwas then concentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c368aed5d7bb4f9cbc810a6899df9373
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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