Pyridine → Benzamide, 2-methyl-N-(5,6,7,8-tetrahydro-1-naphthalenyl)-

HRID 2225134Notes

Reaction equation

HRID 2225134 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18]>C1COCC1>[CH3:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([NH:1][C:2]1[C:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:6]=2[CH:5]=[CH:4][CH:3]=1)=[O:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6115AnilineHCID 702762-Methylbenzoyl chloride

Product 1

HCID 796063Benzamide, 2-methyl-N-(5,6,7,8-tetrahydro-1-naphthalenyl)-Yield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a 25° C. solution of aniline (1 eq) in anhydrous THF (2 mL per mmol aniline) was added polymer bound pyridine (1.5 eq) followed by 2-methyl-benzoyl chloride (1 eq). The mixture was stirred at 25° C. for 12-24 h. The reaction mixture was filtered and the filtrate concentrated in vacuo. Hexane was added to the residue and the resulting precipitate was collected by filtration, resulting in a white solid (yield 65%). LC/MS (M+H)+ m/z 266. The crude material was used without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. additionHexane was added to the residue
  4. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-c37ffd51476f4992b336545363cf7988
Source dataset
uspto-grants-2008_05
Patent number
US07378525B2

Reaction notes

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