Bromine → 5-Bromo-8-methoxy-2-methylquinoline

HRID 2393084Notes

Reaction equation

HRID 2393084 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:13])[CH:9]=[CH:8]2.[Br:14]Br>CO>[Br:14][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([CH3:13])=[N:11]2

Participants

4

Reactant 2

HCID 24408BromineHCID 3169868-Methoxy-2-Methylquinoline

Product 1

HCID 47150215-Bromo-8-methoxy-2-methylquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 8-methoxy-2-methylquinoline (1.0 g) in methanol (30 ml) was treated at room temperature with bromine (0.31 ml). The mixture was heated at 45° C. for 2 hours and the reaction quenched with 5% aqueous sodium metabisulphite (50 ml). The solution was basified with 25% aqueous sodium hydroxide to pH13 and the product extracted with ethyl acetate (2×100 ml). The extracts were combined, dried over magnesium sulphate, filtered and the filtrate evaporated in vacuo. The residue was dissolved in ethyl acetate and passed through a silica pad. The solution was evaporated in vacuo to yield the desired product as an off-white solid (0.43 g).

Workup

  1. customthe reaction quenched with 5% aqueous sodium metabisulphite (50 ml)
  2. extractionthe product extracted with ethyl acetate (2×100 ml)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe filtrate evaporated in vacuo
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. customThe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-f7019cba75f449349a0c7c8c68bde685
Source dataset
uspto-grants-1998_09
Patent number
US05804588

Reaction notes

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