2-Bromopyridine → 4-Methoxy-2'-[hydroxy(2-pyridyl)methyl]benzanilide

HRID 1974117Notes

Reaction equation

HRID 1974117 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[Li].BrC1C=CC=CN=1.C([Li])CCC.[CH3:20][O:21][C:22]1[CH:38]=[CH:37][C:25]([C:26]([NH:28][C:29]2[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=2[CH:31]=[O:32])=[O:27])=[CH:24][CH:23]=1>O1CCCC1.CCCCCC.CCOCC>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([NH:28][C:29]2[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=2[CH:31]([OH:32])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:27])=[CH:37][CH:38]=1

Participants

8

Reactant 4

HCID 79732-BromopyridineHCID 585595N-(2-Formylphenyl)-4-methoxybenzamideHCID 178418339ButyllithiumHCID 178506720HCID 178506720, compound

Product 1

HCID 205600424-Methoxy-2'-[hydroxy(2-pyridyl)methyl]benzanilideYield 46%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Pyridyl lithium, prepared by adding 2-bromopyridine (30.0 g., 0.19 mole) in 200 ml. of ether to 131 ml. of a hexane solution of 1.6 molar n-butyl lithium (0.2 mole) at -70° C., is added in 25 min. to a solution of o-(4-methoxybenzamido)benzaldehyde (8.9 g., 0.035 mole) in 300 ml. of tetrahydrofuran at -25° C. over a 20 min. period with stirring. Stirring is continued for 20 min. at -25° C. 1 hr. at -10° C. and then at 0° C. for 30 min. The reaction mixture is poured into 1500 ml. of cold 1N hydrochloric acid, the aqueous layer separated, washed with ethyl acetate, made strongly basic with concentrated ammonium hydroxide and extracted with ethyl acetate. The ethyl acetate extract is washed with water, brine, dried over sodium sulfate and concentrated and the residue thus obtained triturated with ether to provide a 46% yield of 4-methoxy-2'-[hydroxy(2-pyridyl)methyl]benzanilide, m.p. 127.5° - 128.5° C. (corr.).

Workup

  1. custom1 hr
  2. waitat -10° C. and then at 0° C. for 30 min
  3. additionThe reaction mixture is poured into 1500 ml
  4. customof cold 1N hydrochloric acid, the aqueous layer separated
  5. washwashed with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. extractionThe ethyl acetate extract
  8. washis washed with water, brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated
  11. customthe residue thus obtained
  12. customtriturated with ether

Sources & evidence

ORD record
ord-5793005944274da5bf86f710d495573b
Source dataset
uspto-grants-1976_12
Patent number
US04000143

Reaction notes

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