Bromine → 6-Bromo-2-oxo-1,2-dihydroquinoline-3-carbonitrile

HRID 986005Notes

Reaction equation

HRID 986005 reaction equation
[C:1]([C:3]1[C:4](=[O:13])[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].[Br:14]Br>C(O)(=O)C>[C:1]([C:3]1[C:4](=[O:13])[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([Br:14])=[CH:8][CH:7]=2)#[N:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 27645772-Oxo-1,2-dihydroquinoline-3-carbonitrile

Product 1

HCID 142210276-Bromo-2-oxo-1,2-dihydroquinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A suspension of 3-cyano-2-[1H]-quinolone (13.3 g) in acetic acid (130 cm3) was treated at room temperature with a solution of bromine (4.1 cm3) in acetic acid (10 cm3). After heating under reflux for 4 hours the mixture was cooled to room temperature, filtered, and the solid washed with ethanol to give 3-cyano-6-bromo-2-[1H]-quinolone (14.63 g), a small quantity of which was recrystallised from ethanol, m.p. 308°-311°.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 4 hours the mixture
  3. filtrationfiltered
  4. washthe solid washed with ethanol

Sources & evidence

ORD record
ord-98975366f464408b990f1176354a9b3d
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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