4-Chloroquinazoline → Ethyl 1-quinazolin-4-ylindolin-3-ylacetate

HRID 597041Notes

Reaction equation

HRID 597041 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:13]1>COCCOC>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:13]2)=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 788644-ChloroquinazolineHCID 21795444Ethyl (2,3-dihydro-1H-indol-3-yl)acetate

Product 1

HCID 54457736Ethyl 1-quinazolin-4-ylindolin-3-ylacetate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 4-chloroquinazoline (2.3g.) and ethyl indolin-3-ylacetate (2.6g.) in 1,2-dimethoxyethane (30ml.) was heated under reflux for 15 minutes. The mixture was cooled and filtered, and the solid residue was dissolved in ice-water (40ml.). To the solution was added saturated sodium acetate solution (10ml.), and the mixture was extracted with ethyl acetate (3 × 50ml.). The combined extracts were dried (Na2SO4), and the solvent evaporated in vacuo to give ethyl 1-quinazolin-4-ylindolin-3-ylacetate as a syrup which was proved to be pure by TLC (system A).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 minutes
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. dissolutionthe solid residue was dissolved in ice-water (40ml.)
  6. additionTo the solution was added saturated sodium acetate solution (10ml.)
  7. extractionthe mixture was extracted with ethyl acetate (3 × 50ml.)
  8. dry with materialThe combined extracts were dried (Na2SO4)
  9. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-dcde0069e29d44d29c10c2b03b9f218d
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Reaction notes

Loading…