Methyl Ethyl Ketone → HCID 13532883, compound

HRID 653002Notes

Reaction equation

HRID 653002 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[CH3:13])[N:6]=[CH:5]2.Br[CH:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:16][CH:15]=1)[CH3:13])[N:6]=[CH:5]2

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 20195211HCID 20195211, compound

Product 1

HCID 13532883HCID 13532883, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-[N-(6-chloro-2-quinazolinyl)-N-methylamino]phenol (0.52 g), ethyl 2-bromopropionate (0.40 g), potassium carbonate (0.28 g) and methyl ethyl ketone (25 ml) was heated under reflux for a period of 18 hours. After cooling, the mixture was diluted with water and the aqueous mixture was extracted with dichloromethane. The dichloromethane extract was dried (anhydrous sodium sulfate) and the solvent was removed under reduced pressure. The residue was purified by chromatography over silica gel (eluant dichloromethane) to give ethyl 2-{4-[N-(6-chloro-2-quinazolinyl)-N-methylamino]phenoxy}propionate as a yellow oil. The assigned structure was confirmed by proton magnetic resonance (pmr) spectroscopy and mass spectrometry. Pmr spectrum (CDCl3 ; δ in ppm): 8.93 (1H, s, quinazoline hetero ring proton); 7.60 (3H, s, quinazoline benzo-ring protons); 7.13 (4H, d of d, phenoxy protons); 4.80 (1H, q, CH--CH3); 4.27 (2H, q, CH2 --CH3); 1.60 (3H, d, CH--CH3); 1.27 (3H, t, CH2 --cH3).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for a period of 18 hours
  3. temperatureAfter cooling
  4. extractionthe aqueous mixture was extracted with dichloromethane
  5. extractionThe dichloromethane extract
  6. dry with materialwas dried (anhydrous sodium sulfate)
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by chromatography over silica gel (eluant dichloromethane)

Sources & evidence

ORD record
ord-34742fd74a214b54b59c83d46b9c2a4f
Source dataset
uspto-grants-1987_06
Patent number
US04675047

Reaction notes

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