Ammonia → 4-Hydroxy-3-methoxyphenyl 3-pyridyl ketone

HRID 2260201Notes

Reaction equation

HRID 2260201 reaction equation
Br.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16]CC3C=CC=CC=3)=[C:12]([O:24][CH3:25])[CH:11]=2)=[O:9])[CH:3]=1.N>C(O)(=O)C.C(Cl)Cl>[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([O:24][CH3:25])[CH:11]=2)=[O:9])[CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 260Hydrogen BromideHCID 17977726HCID 17977726, compound

Product 1

HCID 179776754-Hydroxy-3-methoxyphenyl 3-pyridyl ketone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

ca) 50 ml of 33 percent hydrobromic acid in acetic acid are added dropwise within 15 minutes at 10° to 20 g of 4-(benzyloxy)-3-methoxyphenyl 3-pyridyl ketone dissolved in 200 ml of methylene chloride. After stirring at 20° for 3 hours, the reaction mixture is poured into a mixture of 100 ml of conc. aqueous ammonia and ice. The pH is adjusted to 6 by adding acetic acid. The methylene chloride phase is separated: the aqueous phase is extracted twice more with 100 ml of methylene chloride each time. The combined methylene chloride phases are dried over sodium sulfate and evaporated. The residue is recrystallized from methylene chloride/hexane. There is obtained 4-hydroxy-3-methoxyphenyl 3-pyridyl ketone of m.p. 150°-151°.

Workup

  1. customThe methylene chloride phase is separated
  2. extractionthe aqueous phase is extracted twice more with 100 ml of methylene chloride each time
  3. dry with materialThe combined methylene chloride phases are dried over sodium sulfate
  4. customevaporated
  5. customThe residue is recrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-7750079b85e64aaeb0b3cc9aa6ebbb67
Source dataset
uspto-grants-1995_12
Patent number
US05476875

Reaction notes

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