Sulfuric Acid → 5-Bromoquinoline-8-carboxylic acid

HRID 523952

Reaction equation

HRID 523952 reaction equation
[OH:1]S(O)(=O)=O.[Br:6][C:7]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=N2.[OH-:18].[NH4+:19]>O>[Br:6][C:7]1[CH:16]=[CH:15][C:14]([C:17]([OH:1])=[O:18])=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:19]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 47150225-Bromo-8-methylquinoline

Product 1

HCID 592928605-Bromoquinoline-8-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of H2O (80 mL) and H2SO4 (120 mL) at 0° C. was added 5-bromo-8-methylquinoline (25 g, 112.6 mmol). After obtaining a solution, CrO3 was introduced (16 g, 157.6 mmol) in portion wise while maintaining the internal temperature at 70° C. The reaction mixture was stirred for 1 h at 70° C. An additional CrO3 (16 g, 157.6 mmol) was added in portions and stirred at 80° C. for 2.5 h. After completion of the reaction, it was cooled to r.t, poured onto crushed ice, neutralized with aqueous ammonium hydroxide to get the solids. The solids were filtered, dried under high vacuum for 16 h to get the crude 5-bromoquinoline-8-carboxylic acid (28.0 g) as a green colored solid.

Workup

  1. customAfter obtaining a solution, CrO3
  2. additionwas introduced (16 g, 157.6 mmol) in portion wise
  3. stirringstirred at 80° C. for 2.5 h
  4. customAfter completion of the reaction, it
  5. temperaturewas cooled
  6. additionpoured
  7. customonto crushed ice
  8. customto get the solids
  9. filtrationThe solids were filtered
  10. customdried under high vacuum for 16 h

Sources & evidence

ORD record
ord-13fbb75bf1ad426c8829215375de398c
Source dataset
uspto-grants-2016_05
Patent number
US09340509B2

Linked notes

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