Pyridine → HCID 59264627, compound

HRID 645933Notes

Reaction equation

HRID 645933 reaction equation
[N:1]1C=CC=CC=1.Br[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])=O.[NH2:18][C:19]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=O.N1CCCC1>CCO.CN(C1C=CN=CC=1)C>[Cl:27][C:26]1[CH:25]=[CH:24][CH:23]=[C:20]2[C:19]=1[N:18]=[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])[C:8]([NH2:1])=[CH:21]2

Participants

7

Reactant 4

HCID 1049Pyridine2×HCID 31268PyrrolidineHCID 27357852-Bromo-2'-chloroacetophenoneHCID 235104422-Amino-3-chlorobenzaldehyde

Product 1

HCID 59264627HCID 59264627, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
65 °C

Procedure

To pyridine (2.1 ml, 26 mmol) in EtOH (60 ml) was added 2-bromo-1-(2-chlorophenyl)ethanone (6.1 g, 26 mmol) in EtOH (40 ml) dropwise over 10 min. The resulting mixture was heated at 60-70° C. for 1 hour and cooled to room temperature. To the mixture were added pyridine (1.25 ml), 2-amino-3-chlorobenzaldehyde (3.72 g, 24.0 mmol) and DMAP (0.05 g, cat.). The mixture was heated at reflux for 48 hrs. The reaction mixture was cooled to room temperature and pyrrolidine (4.60 ml, 55.0 mmol) was added. After heating at. reflux overnight, the resulting mixture was concentrated. The residue was partitioned between saturated aqueous NaHCO3 and CH2Cl2. The combined organic layers were dried, concentrated. Flash chromatography of the residue over silica gel, using 3:7 EtOAc-hexane, gave 8-chloro-2-(2-chlorophenyl)-quinolin-3-amine, 1H-NMR (DMSO-d6) δ 7.67 (d, J=8.0 Hz, 1H), 7.63 (d, J=8.0 Hz, 1H), 7.50-7.57 (m, 3H), 7.46 (d, J=8.0 Hz, 1H), 7.42 (s, 1H), 7.39 (t, J=8.0 Hz, 1H), 5.32 (br, 2H). Mass Spectrum (ESI) m/e=289.0 (M+1).

Workup

  1. temperaturecooled to room temperature
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 48 hrs
  4. temperatureThe reaction mixture was cooled to room temperature
  5. temperatureAfter heating at
  6. temperaturereflux overnight
  7. concentrationthe resulting mixture was concentrated
  8. customThe residue was partitioned between saturated aqueous NaHCO3 and CH2Cl2
  9. customThe combined organic layers were dried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-aee465bcb01a4f6fa86185d5df060364
Source dataset
uspto-grants-2010_04
Patent number
US07705018B2

Reaction notes

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