4-Hydroxymethylpyridine → 8-methyl-6-[4-(4-pyridylmethoxy)phenyl]-2-(1H)-quinolone

HRID 568346Notes

Reaction equation

HRID 568346 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[CH3:13][C:14]1[CH:15]=[C:16]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)[CH:17]=[C:18]2[C:23]=1[NH:22][C:21](=[O:24])[CH:20]=[CH:19]2.O[CH2:33][C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:13][C:14]1[CH:15]=[C:16]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:33][C:34]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)=[CH:27][CH:26]=2)[CH:17]=[C:18]2[C:23]=1[NH:22][C:21](=[O:24])[CH:20]=[CH:19]2

Participants

6

Reactant 4

HCID 114724-HydroxymethylpyridineHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 201504468-methyl-6-[4-hydroxylphenyl]-2-(1H)-quinolone

Product 1

HCID 201504568-methyl-6-[4-(4-pyridylmethoxy)phenyl]-2-(1H)-quinoloneYield 70.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethylazodicarboxylate (0.189 cm3) in THF (5 cm3) was added at room temperature to a stirred suspension of 8-methyl-6-[4-hydroxyphenyl]-2-(1H)-quinolone (0.25 g), 4-hydroxymethylpyridine (0.109 g) and triphenylphosphine (0.315 g) in THF (10 cm3) under nitrogen. The mixture was heated under reflux for 18 hours, silica (10 g) (Merck "MK 60.9385" [Trade Mark]) was added and voltatile material was removed in vacuo. The residue was placed on top of a silica column (Merck "MK 60.9385" [Trade Mark]) and eluted with ethyl acetate:methanol, 9:1. Combination and evaporation of the appropriate fractions in vacuo gave a solid (0.24 g) which was recrystallised from ethyl acetate-methanol to afford the title compound, m.p. 270.5°-273.5°, (0.08 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. additionsilica (10 g) (Merck "MK 60.9385" [Trade Mark]) was added
  4. customvoltatile material was removed in vacuo
  5. washeluted with ethyl acetate
  6. customCombination and evaporation of the appropriate fractions in vacuo

Sources & evidence

ORD record
ord-4da94508755b42a5aab6bf964508c188
Source dataset
uspto-grants-1988_03
Patent number
US04728654

Reaction notes

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