Sodium hydride → 1,3-Dihydro-3-[7-(2-methoxyethoxy)-4-quinazolinyl]-2H-indol-2-one

HRID 1386274Notes

Reaction equation

HRID 1386274 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[H-].[Na+].Cl[C:14]1[C:23]2[C:18](=[CH:19][C:20]([O:24][CH2:25][CH2:26][O:27][CH3:28])=[CH:21][CH:22]=2)[N:17]=[CH:16][N:15]=1>C1COCC1.CN(C=O)C>[CH3:28][O:27][CH2:26][CH2:25][O:24][C:20]1[CH:19]=[C:18]2[C:23]([C:14]([CH:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][C:2]3=[O:10])=[N:15][CH:16]=[N:17]2)=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 321710OxindoleHCID 10681434HCID 10681434, compound

Product 1

HCID 217172161,3-Dihydro-3-[7-(2-methoxyethoxy)-4-quinazolinyl]-2H-indol-2-oneYield 75%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of oxindole (319 mg, 2.4 mmol) in THF (3 ml) was added dropwise under nitrogen to sodium hydride (58 mg, 2.4 mmol, pre-washed with hexane) and the mixture stirred for 20 minutes at ambient temperature. A solution of 4-chloro-7-(2-methoxyethoxy)quinazoline (191 mg, 0.8 mmol) in DMF (3 ml) was added and the mixture then heated at 70° C. for 1 hour. The mixture was allowed to cool and the solvent removed by evaporation. The mixture was partitioned between water and ether. The aqueous phase was separated and adjusted to pH7 with 2M hydrochloric acid. The resulting solid was collected by filtration and washed with water and ethanol. This solid was then suspended in ether, recollected by filtration, washed with ether and dried under vacuum to give 7(2-methoxyethoxy)-4-(oxindol-3-yl)quinazoline (200 mg, 75%).

Workup

  1. temperaturethe mixture then heated at 70° C. for 1 hour
  2. temperatureto cool
  3. customthe solvent removed by evaporation
  4. customThe mixture was partitioned between water and ether
  5. customThe aqueous phase was separated
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with water and ethanol
  8. filtrationrecollected by filtration
  9. washwashed with ether
  10. customdried under vacuum

Sources & evidence

ORD record
ord-95cdea52369740c69c690acfe41f5262
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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