Potassium Carbonate → HCID 178428841, compound

HRID 2415504Notes

Reaction equation

HRID 2415504 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][C:6]([OH:13])=[CH:7][CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1.CCOC(C)=O.O>CN(C=O)C>[OH:12][C:10]1[C:9]2[C:4](=[CH:5][C:6]([O:13][CH2:21][C:22]3[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=3)=[CH:7][CH:8]=2)[N:3]=[C:2]([CH3:1])[CH:11]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 22728543Water ethylacetateHCID 178428839HCID 178428839, compound

Product 1

HCID 178428841HCID 178428841, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.05 g (10.4 mmol) of 2-methyl-quinoline-4,7-diol, 1.72 g (12.5 mmol) of potassium carbonate and 2.1 g (12.5 mmol) of 4-(bromomethyl)-benzonitrile in 100 ml of DMF were stirred at RT under an nitrogen atmosphere for 4 h until completion of the reaction according to HPLC analysis. The reaction mixture was cooled to RT and poured into EtOAc/water (300 ml/400 ml). The product that precipitated was filtered off by suction, washed with water, AcOEt and ether and dried in a high vacuum to give 2.23 g (73%) of 4-(4-hydroxy-2-methyl-quinolin-7-yloxymethyl)-benzonitrile as a white solid. ISP mass spectrum, m/e: 291.4 (M+1 calculated for C18H14N2O2: 291).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customThe product that precipitated
  3. filtrationwas filtered off by suction
  4. washwashed with water, AcOEt and ether
  5. customdried in a high vacuum

Sources & evidence

ORD record
ord-a33d81a515104fe99174fe711de880ce
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

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