Sodium Hydroxide → 3-Bromo-8-methylquinolin-6-ol

HRID 2421524Notes

Reaction equation

HRID 2421524 reaction equation
N[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[CH:7][C:6]([Br:13])=[CH:5]2.[OH-:14].[Na+]>O.P(=O)(O)(O)O>[Br:13][C:6]1[CH:7]=[N:8][C:9]2[C:4]([CH:5]=1)=[CH:3][C:2]([OH:14])=[CH:11][C:10]=2[CH3:12]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 672141793-Bromo-8-methylquinolin-6-amine

Product 1

HCID 574179313-Bromo-8-methylquinolin-6-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1004Phosphoric AcidSolvent

Conditions

Temperature
180 °C

Procedure

6-Amino-3-bromo-8-methylquinoline (12 g) was suspended in a mixture of water (5 ml) and phosphoric acid (60 ml) and heated in a sealed glass tube to 180° C. for 3 days. The mixture was cooled to ambient temperature, diluted with water then taken to pH 3-4 with aqueous (2M) sodium hydroxide. The precipitate formed was filtered from solution, washed with cold water and sucked to dryness to give 3-bromo-6-hydroxy-8-methylquinoline, 11.0 g, as a grey solid.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customThe precipitate formed
  3. filtrationwas filtered from solution
  4. washwashed with cold water

Sources & evidence

ORD record
ord-96ea333c1b57417fb0607ad44d0bd53b
Source dataset
uspto-grants-2011_06
Patent number
US07956188B2

Reaction notes

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