Pyridine → HCID 23107570, compound

HRID 1094973Notes

Reaction equation

HRID 1094973 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].N1C=CC=CC=1.CO[C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1OC)[C:24](Cl)=[O:25].[CH2:32]([Cl:34])Cl>>[Br:12][C:9]1[CH:10]=[CH:11][C:2]([NH:1][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][CH:29]=[C:21]([CH2:32][Cl:34])[CH:22]=2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 77070Veratroyl chloride2×HCID 736224Methyl 2-amino-5-bromobenzoate2×

Product 1

HCID 23107570HCID 23107570, compound

Procedure

Methyl 2-amino-5-bromobenzoate (compound A) (3.0 g) was dissolved in anhydrous methylene chloride (40.0 ml). Subsequently, pyridine (2.1 ml) and 4-(chloromethyl)benzoyl chloride (compound B) (2.2 ml) were added to the solution at room temperature, and the mixture was stirred at that temperature for one hr. After the completion of the reaction, distilled water was added, followed by separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated to give methyl 5-bromo-2-[3-(chloromethyl)benzoyl]aminobenzoate as a useful intermediate (4.90 g, yield 100%).

Workup

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionfollowed by 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

Sources & evidence

ORD record
ord-ee110e8d1b1040b6b8464c4361847445
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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