Pyridine → HCID 66638013, compound

HRID 1095007Notes

Reaction equation

HRID 1095007 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]1[CH:10]=[C:9]([O:11][CH2:12]COC)[C:8](OCCOC)=[CH:7][C:6]=1[NH2:21])C.N1C=CC=CC=1.[Cl:29][CH2:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34](O)=[O:35]>C(Cl)Cl>[CH3:1][O:3][C:4](=[O:22])[C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[NH:21][C:34](=[O:35])[C:33]1[CH:37]=[CH:38][CH:39]=[C:31]([CH2:30][Cl:29])[CH:32]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 2417523-(Chloromethyl)benzoic acid2×HCID 11347513Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate2×

Product 1

HCID 66638013HCID 66638013, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-5-methoxy-benzoic acid methyl ester (compound A) (2.2 g) produced by the above process was dissolved in anhydrous methylene chloride (40 ml), pyridine (1.5 ml) and 3-(chloromethyl)benzoyl chloride (compound B) (2.1 ml) was added dropwise to the solution at 0° C., and the mixture was then stirred at room temperature for 15 min. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was then subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure to precipitate crystals. The crude crystals were collected by Kiriyama Rohto and was washed with ether to give 2-(3-chloromethyl-benzoylamino)-5-methoxybenzoic acid methyl ester (3.0 g, yield 75%).

Workup

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionat room temperature, and the mixture was then 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 under the reduced pressure
  8. customto precipitate crystals
  9. customThe crude crystals were collected by Kiriyama Rohto
  10. washwas washed with ether

Sources & evidence

ORD record
ord-9fccc1680d2f4ad0911e701cea7a335e
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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