Dimethylformamide → N-[4-(hydroxymethyl)phenyl]-7-phenyl-3,4-dihydronaphthalene-2-carboxamide

HRID 1387780Notes

Reaction equation

HRID 1387780 reaction equation
[C:1]1([C:7]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][C:13]([C:17]([OH:19])=O)=[CH:14]3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20](Cl)(=O)[C:21](Cl)=O.C[N:27]([CH:29]=O)C.[CH2:31]1[CH2:35][O:34][CH2:33][CH2:32]1>>[OH:34][CH2:33][C:32]1[CH:31]=[CH:35][C:29]([NH:27][C:17]([C:13]2[CH2:12][CH2:11][C:10]3[C:15](=[CH:16][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:8][CH:9]=3)[CH:14]=2)=[O:19])=[CH:21][CH:20]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 106344227-phenyl-3,4-dihydronaphthalene-2-carboxylic Acid

Product 1

HCID 10641929N-[4-(hydroxymethyl)phenyl]-7-phenyl-3,4-dihydronaphthalene-2-carboxamide

Procedure

In THF (10 ml) was dissolved 7-phenyl-3,4-dihydronaphthalene-2-carboxylic acid (500 mg), and to the solution were added oxalyl chloride (262 μl) and a drop of DMF. The mixture was stirred at room temperature for 1 hour and concentrated under reduced pressure. The residue was dissolved in DMF (5 mL), and to the mixture was dropwise added a solution of 4-aminobenzylalcohol (246 mg) in pyridine (10 ml) at 0° C. The reaction mixture was stirred at 0° C. for 3 hours. To the mixture was added water (500 ml), and then the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-acetone to give N-[4-(hydroxymethyl)phenyl]-7-phenyl-3,4-dihydronaphthalene-2-carboxamide (486 mg) as pale brown crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in DMF (5 mL)
  3. additionto the mixture was dropwise added a solution of 4-aminobenzylalcohol (246 mg) in pyridine (10 ml) at 0° C
  4. stirringThe reaction mixture was stirred at 0° C. for 3 hours
  5. additionTo the mixture was added water (500 ml)
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with saturated sodium chloride solution
  8. dry with materialdried with anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was recrystallized from ethyl acetate-acetone

Sources & evidence

ORD record
ord-53c58544d26f4d408aefb6252f1c13d3
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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