Bromine → 8-benzyloxy-5-bromo-3-methyl-1H-quinolin-2-one

HRID 1162369Notes

Reaction equation

HRID 1162369 reaction equation
[Br:1]Br.[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:20]=1[NH:19][C:18](=[O:21])[C:17]([CH3:22])=[CH:16]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([Br:1])=[C:15]2[C:20]=1[NH:19][C:18](=[O:21])[C:17]([CH3:22])=[CH:16]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 224992238-Benzyloxy-3-methyl-1H-quinolin-2-one

Product 1

HCID 224992118-benzyloxy-5-bromo-3-methyl-1H-quinolin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (0.57 g) in acetic acid (2 mL) is added dropwise to a solution of 8-benzyloxy-3-methyl-1H-quinolin-2-one (0.94 g) and sodium acetate (0.96 g) in acetic acid (12 mL) at room temperature. The reaction mixture is stirred at room temperature for 3 hours, evaporated, the residue partitioned between water (5 mL) and ethyl acetate (5 mL), extracting a further 2× with ethyl acetate (5 mL). Combined organic extracts are dried over magnesium sulphate and purified by flash column chromatography on silica gel, eluting with 2% methanol in dichloromethane.

Workup

  1. customevaporated
  2. customthe residue partitioned between water (5 mL) and ethyl acetate (5 mL)
  3. extractionextracting a further 2× with ethyl acetate (5 mL)
  4. dry with materialCombined organic extracts are dried over magnesium sulphate
  5. custompurified by flash column chromatography on silica gel
  6. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-d6819b49f5fe42a9af5e3fc4b23d79f5
Source dataset
uspto-grants-2010_10
Patent number
US07820694B2

Reaction notes

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