Hydrogen Bromide → HCID 21459131, compound

HRID 274559Notes

Reaction equation

HRID 274559 reaction equation
Br.[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20]CC3C=CC=CC=3)=[C:16]([O:28][CH3:29])[CH:15]=2)=[O:13])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>C(O)(=O)C.C(Cl)Cl>[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([O:28][CH3:29])[CH:15]=2)=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 21459146HCID 21459146, compound

Product 1

HCID 21459131HCID 21459131, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

15 ml of 33 percent hydrobromic acid in glacial acetic acid are added dropwise within 5 minutes at room temperature to 7.5 g of 4-(benzyloxy)-3-methoxyphenyl 4-quinolyl ketone dissolved in 150 ml of methylene chloride. After stirring at 20° for 4.5 hours, the reaction mixture is poured portionwise into 250 ml of saturated sodium bicarbonate solution. The methylene chloride phase is separated; the aqueous phase is extracted twice 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 4-quinolyl ketone of m.p. 190°-192°.

Workup

  1. customThe methylene chloride phase is separated
  2. extractionthe aqueous phase is extracted twice 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-478e4e23dd35416298f1d0f2c9f5344c
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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