Pyridine → 3-(3-Chloromethylbenzoylamino)-naphthalene-2-carboxylic acid methyl ester

HRID 1095001Notes

Reaction equation

HRID 1095001 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5]1C=C(N2CCCCC2)C=CC=1N)C.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl:25][CH2:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30]([OH:32])=O>C(Cl)Cl>[CH3:1][O:3][C:4]([C:5]1[C:24]([NH:19][C:30](=[O:32])[C:29]2[CH:33]=[CH:34][CH:35]=[C:27]([CH2:26][Cl:25])[CH:28]=2)=[CH:23][C:22]2[C:21](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:20]=1)=[O:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 2417523-(Chloromethyl)benzoic acid2×HCID 613065672-Amino-5-piperidin-1-yl-benzoic acid ethyl ester2×

Product 1

HCID 666381163-(3-Chloromethylbenzoylamino)-naphthalene-2-carboxylic acid methyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Amino-naphthalene-2-carboxylic acid methyl ester (compound A) (530 mg) produced by the above process was dissolved in anhydrous methylene chloride (10 ml). Pyridine (0.5 ml) and 3-(chloromethyl)benzoyl chloride (compound B) (0.6 ml) was added dropwise to the solution at room temperature, and the mixture was then stirred at that temperature for 30 min. After the completion of the reaction, distilled water was added thereto at room temperature, 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 concentrated under the reduced pressure to precipitate crystals. The crystals were collected by Kiriyama Rohto and were washed with a hexane-ether solvent to give 3-(3-chloromethylbenzoylamino)-naphthalene-2-carboxylic acid methyl ester (870 mg, yield 93%).

Workup

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionat room temperature, and the 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 concentrated under the reduced pressure
  8. customto precipitate crystals
  9. customThe crystals were collected by Kiriyama Rohto
  10. washwere washed with a hexane-ether solvent

Sources & evidence

ORD record
ord-ca3b019a00dc4bcb9db83d42d3e35795
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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