Bromine → 6-Bromo-3,4-dihydro-4-methyl-2(1H)-quinolinone

HRID 986017Notes

Reaction equation

HRID 986017 reaction equation
[Br:1]Br.[CH3:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6](=[O:14])[CH2:5]1>C(O)(=O)C>[Br:1][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:14])[CH2:5][CH:4]2[CH3:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 52461484-methyl-3,4-dihydro-1H-quinolin-2-one

Product 1

HCID 201589746-Bromo-3,4-dihydro-4-methyl-2(1H)-quinolinone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (0.08 cm3) in acetic acid (1 cm3) was added at room temperature to a stirred solution of 4-methyl-3,4-dihydro-2-(1H)-quinolone (0.5 g) in acetic acid (4.0 cm3). After 2 hours, volatile material was removed in vacuo, the residue was partitioned between chloroform (50 cm3) and water (20 cm3), and the organic phase was further extracted with chloroform (2×20 cm3). The combined and dried (MgSO4) organic extracts were evaporated in vacuo and the solid residue was recrystallised from ethyl acetate to afford 6-bromo-4-methyl-3,4-dihydro-2-(1H)-quinolone, m.p. 190°, (0.35 g).

Workup

  1. customvolatile material was removed in vacuo
  2. customthe residue was partitioned between chloroform (50 cm3) and water (20 cm3)
  3. extractionthe organic phase was further extracted with chloroform (2×20 cm3)
  4. dry with materialdried (MgSO4) organic extracts
  5. customwere evaporated in vacuo
  6. customthe solid residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-7553d1d884034a6e93dc5b31500d4c53
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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