Ethanol → Benzo[h]quinoline-2-carbaldehyde

HRID 868954Notes

Reaction equation

HRID 868954 reaction equation
Br[CH:2](Br)[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]3[CH:16]=[CH:15][CH:14]=[CH:13][C:7]3=[CH:8][CH:9]=2)[N:4]=1.CC[OH:20]>C1COCC1.O.[N+]([O-])([O-])=O.[Ag+]>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]3[CH:13]=[CH:14][CH:15]=[CH:16][C:6]3=2)[CH:11]=[CH:12][C:3]=1[CH:2]=[O:20]

Participants

6

Reactant 2

HCID 702EthanolHCID 70097431Benzo[h]quinoline, 2-(dibromomethyl)-

Product 1

HCID 15148223Benzo[h]quinoline-2-carbaldehyde

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-(dibromomethyl)benzo[h]quinoline (52 mg, 0.148 mmol) in EtOH (2 mL) and THF (1 mL) was added a solution of AgNO3 (75 mg, 0.444 mmol) in H2O (1 mL). The mixture was stirred at reflux for 2 h. The solid was filtered off and the organic solvent was removed under reduced pressure. DCM (5 mL) was added and the layers were separated. The aqueous layer was extracted with DCM (5 mL×2). The combined organic layers were washed with brine (2 mL) and dried by anhydrous Na2SO4. The organic layer was concentrated to give benzo[h]quinoline-2-carbaldehyde (30 mg) as a yellow solid.

Workup

  1. temperatureat reflux for 2 h
  2. filtrationThe solid was filtered off
  3. customthe organic solvent was removed under reduced pressure
  4. additionDCM (5 mL) was added
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with DCM (5 mL×2)
  7. washThe combined organic layers were washed with brine (2 mL)
  8. dry with materialdried by anhydrous Na2SO4
  9. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-092856d08fd44423a79cf637a44707ac
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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