Ammonium Hydroxide → 6-Bromo-4-chloro-8-methylquinoline

HRID 1952297Notes

Reaction equation

HRID 1952297 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2O.P(Cl)(Cl)([Cl:16])=O.[OH-].[NH4+]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[Cl:16]

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 178422426HCID 178422426, compound

Product 1

HCID 435319436-Bromo-4-chloro-8-methylquinolineYield 95%

Procedure

A mixture of 6-bromo-8-methyl-4-quinolinol (1.42 g, 5.95 mmol) and phosphorous oxychloride (10.95 g, 71.40 mmol) was heated at reflux for 1 h, cooled, poured onto ice, and neutralized by addition of 30% ammonium hydroxide. The resulting solid was filtered and dried in a vacuum oven to give the title compound (1.45 g, 95%) as a tan solid. MS(ES)+ m/e 256 [M+H].

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. temperaturecooled
  4. additionpoured onto ice
  5. filtrationThe resulting solid was filtered
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-1395e7ddb8d948a1bb540850b26c5c24
Source dataset
uspto-grants-2013_03
Patent number
US08404837B2

Reaction notes

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