Ammonium Hydroxide → 6-Fluoro-2-methylquinolin-7-ol

HRID 338929Notes

Reaction equation

HRID 338929 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12]C)[N:8]=[C:7]([CH3:14])[CH:6]=[CH:5]2.[NH4+].[OH-]>Br>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[N:8]=[C:7]([CH3:14])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 867074426-Fluoro-7-methoxy-2-methylquinoline

Product 1

HCID 1363380756-Fluoro-2-methylquinolin-7-olYield 133.7%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

6-Fluoro-7-methoxy-2-methylquinoline (5.2 g, 19 mmol) was heated to reflux in 48% aqueous HBr for 48 hours. After cooling, the reaction was basified (pH 8) by addition of NH4OH. The resulting solid was filtered, washed with water and dried to yield 6-fluoro-2-methylquinolin-7-ol (4.5 g, 93% yield) as a black solid.

Workup

  1. temperatureAfter cooling
  2. filtrationThe resulting solid was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-be71dbd7ade54710992c9e16f73af80b
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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