Water → HCID 178515333, compound

HRID 228843Notes

Reaction equation

HRID 228843 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]=O)=[O:4].[OH2:14].[OH-].[K+]>CO>[OH:4][C:3]1[C:2]([OH:14])=[CH:12][C:7]2[C:6](=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 125333492-chloro-N-(2-formylphenyl)acetamide

Product 1

HCID 178515333HCID 178515333, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chloro-N-(2-formyl-phenyl)-acetamide (960 mg) was dissolved in a mixed solvent composed of water (60 ml) and methanol (24 ml) at 100° C. A 10% aqueous potassium hydroxide solution (12 ml) was added dropwise to the solution and was then heated under reflux for one hr. The reaction solution was cooled to room temperature, methanol was then removed under the reduced pressure, and the residue was neutralized with a 1 N aqueous hydrochloric acid solution. The precipitate was collected by filtration, was washed with ethyl acetate, and was dried under the reduced pressure to give 2,3-dihydroxyquinoline (450 mg, yield 26%).

Workup

  1. temperaturewas then heated
  2. temperatureunder reflux for one hr
  3. custommethanol was then removed under the reduced pressure
  4. filtrationThe precipitate was collected by filtration
  5. washwas washed with ethyl acetate
  6. customwas dried under the reduced pressure

Sources & evidence

ORD record
ord-27f5f90fd7a34abe8750f71f1d17c618
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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