3-Quinolinecarboxaldehyde → HCID 46841409, compound

HRID 1846334Notes

Reaction equation

HRID 1846334 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=O)[CH:2]=1.[NH2:13][C:14]1[CH:29]=[CH:28][CH:27]=[CH:26][C:15]=1[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=[O:17]>CCO>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([N:18]2[C:16](=[O:17])[C:15]3[C:14](=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:13]=[C:11]2[C:3]2[CH:2]=[N:1][C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 836413-QuinolinecarboxaldehydeHCID 6704722-amino-N-(4-chlorophenyl)benzamide

Product 1

HCID 46841409HCID 46841409, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Quinoline carboxaldehyde (0.41 mmol) and anhydrous CuCl2 (0.110 g, 0.82 mmol) were added to a solution of 2-amino-N-(4-chlorophenyl)benzamide (0.100 g, 0.41 mmol) in anhydrous EtOH (10 mL). The mixture was heated at reflux temperature for 4 hours and concentrated in vacuo. The residue was dissolved in EtOAc and washed with H2O and brine, dried (Na2SO4), filtered, and concentrated. Purification by flash chromatography on silica gel, eluting with 5% to 50% EtOAc in heptane, afforded the title compound as a white solid (14%). 1H-NMR (300 MHz, DMSO-d6): δ 8.83 (d, J=2.1 Hz, 1H), 8.45 (d, J=1.8 Hz, 1H), 8.24 (d, J=8.0 Hz, 1H), 7.88-8.03 (m, 3H), 7.74-7.88 (m, 2H), 7.56-7.73 (m, 2H), 7.52 (d, J=8.6 Hz, 2H), 7.40 (d, J=8.7 Hz, 2H). MS (APCI) m/z: 384 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 4 hours
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with H2O and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash chromatography on silica gel
  10. washeluting with 5% to 50% EtOAc in heptane

Sources & evidence

ORD record
ord-c00c208a00854ef5b3f0b7324fce4001
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

Loading…