Water → HCID 14303742, compound

HRID 2350967Notes

Reaction equation

HRID 2350967 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][C:13](=[O:16])[C:14]=2[CH3:15])=[CH:5][CH:4]=1.B(Br)(Br)Br.O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][C:13](=[O:16])[C:14]=2[CH3:15])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 14303731HCID 14303731, compound

Product 1

HCID 14303742HCID 14303742, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 300 ml of a solution of 18.7 g (0.051 mole) of 2-(4-methoxyphenyl)-3-methyl-1,6-diphenyl-4(1H)-pyridinone in methylene chloride, 25.0 g (0.010 mole) of boron tribromide was added dropwise. After stirring the resultant mixture at room temperature for 15 hours, the reaction mixture was poured into water, followed by neutralization with sodium hydrogen carbonate. Deposited crystals were collected by filtration and washed with aceton, thereby affording 16.9 g of 2-(4-hydroxyphenyl)-3-methyl-1,6-diphenyl-4(1H)-pyridinone having a melting point of not lower than 300° C.

Workup

  1. filtrationDeposited crystals were collected by filtration
  2. washwashed with aceton

Sources & evidence

ORD record
ord-944a692152ab4533bb92fd8f061f7795
Source dataset
uspto-grants-1989_10
Patent number
US04871751

Reaction notes

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