5-Acetyl-8-(benzyloxy)-1,2-dihydroquinolin-2-one → 8-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline

HRID 1472735Notes

Reaction equation

HRID 1472735 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:22])[NH:9]2)(=[O:3])[CH3:2].[Br-:23].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CO>[CH2:15]([O:14][C:11]1[CH:12]=[CH:13][C:4]([C:1](=[O:3])[CH2:2][Br:23])=[C:5]2[C:10]=1[NH:9][C:8](=[O:22])[CH:7]=[CH:6]2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 133754445-Acetyl-8-(benzyloxy)-1,2-dihydroquinolin-2-oneHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 116678678-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinolineYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 5-acetyl-8-(benzyloxy)quinolin-2(1H)-one (19.4 g, 66.4 mmol) in anhydrous THF (240 mL) and anhydrous methanol (165 mL), a solution of tetra-n-butylammonium tribromide (54.5 g, 113.0 mmol) in anhydrous THF (130 mL) was added dropwise over 1.5 hours. The resultant solution was stirred at RT overnight before concentrating under reduced pressure without heating. The residue was re-dissolved in methanol (200 mL). Saturated aqueous ammonium chloride solution (390 mL) was added with ice-cooling. The resultant suspension was filtered, and the solid was washed with water and dried under vacuum. The solid was suspended in dichloromethane and methanol (1:1 v/v, 100 mL) for 90 minutes. The solid was collected by filtration, washed with dichloromethane and air-dried to afford the title compound (18.0 g, 73%).

Workup

  1. concentrationbefore concentrating under reduced pressure
  2. temperaturewithout heating
  3. dissolutionThe residue was re-dissolved in methanol (200 mL)
  4. additionSaturated aqueous ammonium chloride solution (390 mL) was added with ice-
  5. temperaturecooling
  6. filtrationThe resultant suspension was filtered
  7. washthe solid was washed with water
  8. customdried under vacuum
  9. filtrationThe solid was collected by filtration
  10. washwashed with dichloromethane
  11. customair-dried

Sources & evidence

ORD record
ord-15176ba80ff64ad59de85e98193317ff
Source dataset
uspto-grants-2015_04
Patent number
US09012644B2

Reaction notes

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