Water → HCID 22132809, compound

HRID 1857226Notes

Reaction equation

HRID 1857226 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[N:21]=[CH:20][CH:19]=[C:18]2Cl.O>C1(C)C=CC=CC=1>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[N:21]=[CH:20][CH:19]=[C:18]2[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[C:9]#[N:10]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27914Benzeneacetonitrile, 4-bromo-HCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 22132809HCID 22132809, compoundYield 22.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

Commercially available 4-bromophenylacetonitrile (4.3 g) was dissolved in toluene (10 ml) and the temperature was lowered to 0° C., after which sodium hydride (1.0 g) was added, the temperature was raised to 50° C., and the admixture was then stirred for 1 hour. Next, 6,7-dimethoxy-4-chloroquinoline (2.2 g) was added, and the admixture was stirred for 15 hours, after which water was poured and the mixture was extracted with ethyl acetate. After drying with anhydrous sodium sulfate and removing the solvent by distillation, the resulting residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (2/1) to obtain 850 mg of the title compound (yield: 22%).

Workup

  1. customwas lowered to 0° C.
  2. stirringthe admixture was stirred for 15 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialAfter drying with anhydrous sodium sulfate
  5. customremoving the solvent
  6. distillationby distillation
  7. customthe resulting residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (2/1)

Sources & evidence

ORD record
ord-1f90a79258dd4c9998f5377a9225e1e0
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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