Tetrahydrofuran → N-{2-[1-Hydroxy-1-(pyridin-2-yl)ethyl]phenyl}-4-methoxybenzamide

HRID 1974120Notes

Reaction equation

HRID 1974120 reaction equation
C[Li].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:11]1[CH:27]=[CH:26][CH:25]=[CH:24][C:12]=1[NH:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)=[O:10].O1CCC[CH2:29]1>C1C=CC=CC=1.CCCCCC>[OH:10][C:9]([C:11]1[CH:27]=[CH:26][CH:25]=[CH:24][C:12]=1[NH:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=1)[CH3:29]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 205600054-Methoxy-N-[2-(pyridine-2-carbonyl)phenyl]benzamideHCID 178418348HCID 178418348, compound

Product 1

HCID 20560094N-{2-[1-Hydroxy-1-(pyridin-2-yl)ethyl]phenyl}-4-methoxybenzamide

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8058HexaneSolvent

Procedure

Methyl lithium (0.24 mole, 142 ml. of 1.7 molar in ether) is added to 2'-(2-pyridinecarbonyl)-p-anisanilide (36.6 g., 0.11 mole) in 400 ml. of tetrahydrofuran in 15 min. with stirring at 10° -20° C. Stirring is continued for another 30 min., the reaction mixture hydrolyzed by addition of 300 ml. of water, concentrated under reduced pressure until the tetrahydrofuran solvent is substantially removed, and the mixture extracted with ethyl acetate. The ethyl acetate extract washed with water, brine, dried over sodium sulfate and concentrated affords a residual dark brown oil. The residue taken up in benzene and diluted with hexane affords 2'-[1-hydroxy-1-(2-pyridyl)ethyl] -p-anisanilide, m.p. 127° -128° C., from aqueous-methanol.

Workup

  1. additionthe reaction mixture hydrolyzed by addition of 300 ml
  2. concentrationof water, concentrated under reduced pressure until the tetrahydrofuran solvent
  3. customis substantially removed
  4. extractionthe mixture extracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwashed with water, brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customaffords a residual dark brown oil

Sources & evidence

ORD record
ord-31cb850436c744babc3fe98053ebeaf4
Source dataset
uspto-grants-1976_12
Patent number
US04000143

Reaction notes

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