Acetone → 8-Bromo-2-methylquinoline-4-carboxylic acid

HRID 47433Notes

Reaction equation

HRID 47433 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[C:7]2=O.[OH-:13].[Na+].Cl.[CH3:16][C:17]([CH3:19])=O>O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]=[C:17]([CH3:19])[CH:16]=[C:7]2[C:8]([OH:11])=[O:13]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23023537-Bromoisatin

Product 1

HCID 40398258-Bromo-2-methylquinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 7-bromoisatin (6.0 g) in acetone (27 ml) was treated with sodium hydroxide (4.6 g) in water (23 ml). The mixture was heated to reflux for 8 h, cooled and solvent reduced in volume at reduced pressure to approx. 25 ml. The residual aqueous phase was acidified with conc. HCl, extracted with ethyl acetate, the organic phase dried (MgSO4) and solvent removed at reduced pressure to give the title compound (7.2 g) as a yellow solid. 1H NMR δ: 2.85 (3H, s), 7.40 (1H, m), 7.90 (1H, s), 8.05 (1H, dd, J=1.2, 7.6 Hz), 8.79 (1H, dd, J=1.0, 8.5 Hz).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 8 h
  3. temperaturecooled
  4. extractionextracted with ethyl acetate
  5. dry with materialthe organic phase dried (MgSO4) and solvent
  6. customremoved at reduced pressure

Sources & evidence

ORD record
ord-dddd98b2ce31492ab417c1f24b1dcb52
Source dataset
uspto-grants-2004_03
Patent number
US06699879B1

Reaction notes

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