Dichloromethane → Acenaphtho[1,2-b]quinoline-10-carbaldehyde

HRID 1089296Notes

Reaction equation

HRID 1089296 reaction equation
[CH:1]1[CH:10]=[CH:9][C:8]2[C:3]3=[C:4]([C:11]4[C:20]([C:2]=13)=[CH:19][C:18]1[CH:17]=[C:16]([CH2:21][OH:22])[CH:15]=[CH:14][C:13]=1[N:12]=4)[CH:5]=[CH:6][CH:7]=2.[Mn]([O-])([O-])(=O)=O.[Ba+2].C(Cl)Cl>CCOC(C)=O.C1COCC1>[CH:1]1[CH:10]=[CH:9][C:8]2[C:3]3=[C:4]([C:11]4[C:20]([C:2]=13)=[CH:19][C:18]1[CH:17]=[C:16]([CH:21]=[O:22])[CH:15]=[CH:14][C:13]=1[N:12]=4)[CH:5]=[CH:6][CH:7]=2

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 3084030Barium manganateHCID 14555906Acenaphtho[1,2-b]quinoline-10-methanol

Product 1

HCID 14555869Acenaphtho[1,2-b]quinoline-10-carbaldehydeYield 71.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a RB flask equipped with magnetic stirring bar, reflux condenser, N2 inlet line with bubbler was added acenaphtho[1,2-b]quinoline-10-methanol (14A, 2.25 g, 8 mmol), barium manganate (Aldrich, 4.0 g, 16 mmol) and dry CH2Cl2 (1 L). The mixture was refluxed for 24 h, filtered and the resulting dark yellow solution filtered and the solvent removed by rotary evaporation to give a dark green solid. This material was dissolved in a mixture of EtOAc (700 mL) and THF (200 mL) and passed through a small plug of SiO2 using EtOAc as the eluting solvent. The appropriate fractions were combined and the solvent removed by rotary evaporation to give a 71.7% yield of acenaphtho[1,2-b]quinoline-10-carbaldehyde, mp 245°-246°, (C,H,N).

Workup

  1. customTo a RB flask equipped with magnetic stirring bar
  2. temperaturereflux condenser, N2 inlet line with bubbler
  3. temperatureThe mixture was refluxed for 24 h
  4. filtrationfiltered
  5. filtrationthe resulting dark yellow solution filtered
  6. customthe solvent removed by rotary evaporation
  7. customto give a dark green solid
  8. customthe solvent removed by rotary evaporation

Sources & evidence

ORD record
ord-fdf5efbfbbf643ac9cf3de478f4559dc
Source dataset
uspto-grants-1990_10
Patent number
US04965285

Reaction notes

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