Tetrahydrofuran → 2-[2-(4-Methoxyphenyl)-2-hydroxyethenyl]-n-methylnicotinamide

HRID 1006928Notes

Reaction equation

HRID 1006928 reaction equation
[CH3:1][C:2]1[N:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].C([N-]C(C)C)(C)C.[Li+].[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#N)=[CH:24][CH:23]=1.[O:30]1CCCC1>C1CCCCC1>[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]([OH:30])=[CH:1][C:2]2[N:11]=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([NH:6][CH3:7])=[O:5])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 701294-MethoxybenzonitrileHCID 2724682Lithium diisopropylamideHCID 12833322N,2-Dimethyl-3-pyridinecarboxamide

Product 1

HCID 1371829882-[2-(4-Methoxyphenyl)-2-hydroxyethenyl]-n-methylnicotinamide

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
-78 °C

Procedure

2-Methyl-N-methylnicotinamide (4.505 g) was dissolved in tetrahydrofuran (150 ml), followed by the dropwise addition of a solution of 1.5M lithium diisopropylamide in cyclohexane (40 ml) in nitrogen atmosphere at −30 to −20° C., and the mixture was stirred for 50 min. After cooling to −78° C., 4-methoxybenzonitrile (3.995 g)/tetrahydrofuran solution (20 ml) was added dropwise thereinto. After the mixture was stirred for 1 hr as it was, the cooling bath was removed, and then it was stirred overnight. An aqueous solution of saturated ammonium chloride was added thereto, and then the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. A small amount of ethyl acetate was added to the resulting residue, and then the resulting insoluble matters were collected by filtration, to give 5.395 g of the title compound as a yellow solid.

Workup

  1. stirringAfter the mixture was stirred for 1 hr as it
  2. customthe cooling bath was removed
  3. stirringit was stirred overnight
  4. additionAn aqueous solution of saturated ammonium chloride was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe resulting organic layer was washed with water
  7. dry with materialdried (over MgSO4)
  8. customevaporated
  9. additionA small amount of ethyl acetate was added to the resulting residue
  10. filtrationthe resulting insoluble matters were collected by filtration

Sources & evidence

ORD record
ord-d8c621bf9fd14ada9725b20665bccc25
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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