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

HRID 1726521Notes

Reaction equation

HRID 1726521 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 imnol 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-b3c0d7d3a28d4d84b0720b7629d2d6f1
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

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