Water → 4-(Quinolin-2-ylmethoxy)benzamide

HRID 33888

Reaction equation

HRID 33888 reaction equation
Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[OH:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[CH2:2][O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 203942-(Chloromethyl)quinolineHCID 650524-Hydroxybenzamide

Product 1

HCID 440880074-(Quinolin-2-ylmethoxy)benzamideYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-Chloromethyl-quinoline (1.57 g) and 4-Hydroxy-benzamide (995 mg) in dimethyl formamide (20 mL) was added cesium carbonate (7.3 g) and the reaction mixture heated at 80° C. for 18 h. The reaction mixture was poured into water and extracted with chloroform, dried magnesium sulfate, filtered and concentrated to provided the title compound (909 mg). MS: (M+H -m/z=279.3).

Workup

  1. extractionextracted with chloroform, dried magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bc33918c6f2f4e24aaf97b29e1ba3cc7
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Linked notes

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