3-Bromophenol → HCID 10221666, compound

HRID 1934933Notes

Reaction equation

HRID 1934933 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.Cl[C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][C:13]=1[C:26]#[N:27]>[OH-].[Na+]>[Br:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][C:13]=1[C:26]#[N:27]

Participants

5

Reactant 3

HCID 115633-BromophenolHCID 14797Potassium HydroxideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 10221666HCID 10221666, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 0.16 g of 88% KOH and 1.73 g of 3-bromophenol at 50° C. was treated with 0.50 g of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile. The resulting mixture was heated to 170° C. during 30 min, cooled, and treated at 0° C. with 40 ml of 0.1N NaOH. The solid which resulted was filtered, washed with water, and dissolved in methylene chloride. The solution was washed with 0.5 N NaOH and water, dried, and concentrated. The resulting solid was recrystallized from methylene chloride-hexane to give 4-(3-bromophenoxy)-6,7-dimethoxy-3-quinolinecarbonitrile as a white solid, mp 187-190° C.

Workup

  1. temperaturecooled
  2. customThe solid which resulted
  3. filtrationwas filtered
  4. washwashed with water
  5. dissolutiondissolved in methylene chloride
  6. washThe solution was washed with 0.5 N NaOH and water
  7. customdried
  8. concentrationconcentrated
  9. customThe resulting solid was recrystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-8cbb1396ece64822a2f868c26d9ffc97
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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