Dimethylformamide → HCID 24266067, compound

HRID 2099297Notes

Reaction equation

HRID 2099297 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([Cl:14])=[CH:7][CH:8]=2)[N:3]=1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-:27][Cr](O[Cr]([O-])(=O)=O)(=O)=O.CN(C=O)C>O>[Cl:1][C:2]1[C:11]([C:12]([OH:27])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([Cl:14])=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2724130Cornforth reagentHCID 111388162,7-Dichloroquinoline-3-carboxaldehyde

Product 1

HCID 24266067HCID 24266067, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A dry reaction flask equipped with a magnetic stirring bar and a rubber septum was charged with 2,7-dichloro-3-formylquinoline 3 (1.1 g, 5 mmol), PDC (3.76 g, 10 mmol) and dry DMF (5 mL) and stirred at room temperature for 24 h. The reaction mixture was diluted with water (500 mL), filtered, the filtrate was saturated with NaCl and the resulting aqueous solution was extracted with EtOAc (3×200 mL). The EtOAc extract was dried over anhydrous Na2SO4 and solvent was removed to give 1.02 g (85%) of the desired 2,7-dichloroquinoline-3-carboxylic acid 4. TLC Rf: 0.12 (20% MeOH/EtOAc); 1H NMR (acetone d6): 8.96 (s, 1H); 8.22 (d, 1H, J=9.0 Hz), 8.04 (d, 1H, J=1.8 Hz), 7.97 (bs, 1H), 7.74 (dd, 1H, J=1.8 and 8.7 Hz); LCMS (ret. time): 25.15 min.; MS (m/z): 241 (MH+).

Workup

  1. customA dry reaction flask
  2. customequipped with a magnetic stirring bar
  3. filtrationfiltered
  4. extractionthe resulting aqueous solution was extracted with EtOAc (3×200 mL)
  5. extractionThe EtOAc extract
  6. dry with materialwas dried over anhydrous Na2SO4 and solvent
  7. customwas removed

Sources & evidence

ORD record
ord-137e82249b774bb79257f839eb27c18b
Source dataset
uspto-grants-2009_08
Patent number
US07569580B2

Reaction notes

Loading…