Water → 4-(4-Phenylphenyloxy)-6-quinolinecarboxylic acid

HRID 1072877Notes

Reaction equation

HRID 1072877 reaction equation
[H-].[Na+].[C:3]1([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:27]([O:29]C)=[O:28])[CH:25]=2)[N:20]=[CH:19][CH:18]=1.O>CC1(C)NC=NC1=O>[C:3]1([C:9]2[CH:10]=[CH:11][C:12]([O:15][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:27]([OH:29])=[O:28])[CH:25]=4)[N:20]=[CH:19][CH:18]=3)=[CH:13][CH:14]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 71034-HydroxybiphenylHCID 24758Sodium hydrideHCID 16112718Methyl 4-bromoquinoline-6-carboxylate

Product 1

HCID 223877994-(4-Phenylphenyloxy)-6-quinolinecarboxylic acidYield 56.9%

Reagents, catalysts & solvents 1

HCID 178430617HCID 178430617, compoundSolvent

Procedure

60% Sodium hydride (38 mg) was suspended in dimethylimidazolinone (1 ml). 4-Phenylphenol (160 mg) was added while stirring under water-cooling, and the mixture was stirred under water-cooling for 0.5 hr. Methyl 4-bromo-6-quinolinecarboxylate (100 mg) was added under water-cooling and the mixture was stirred at 100° C. for 5 hr, and then at 140° C. for 3 hr. Water (10 ml) was added to the reaction mixture and the mixture was extracted once with ethyl acetate. The aqueous layer was made adjusted to pH 4 with 1N hydrochloric acid and the resulting solid was collected by filtration to give the object compound (73 mg) as a pale brown powder.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred under water-
  3. temperaturecooling for 0.5 hr
  4. temperaturecooling
  5. stirringthe mixture was stirred at 100° C. for 5 hr
  6. extractionthe mixture was extracted once with ethyl acetate
  7. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-2b06ad7b0dd54aa9ae916caae51487e4
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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