Dimethylformamide → Ethyl 1-(7chloroquinazolin-4-yl)-2-methyl-5-n-propoxyindol-3-ylacetate

HRID 597059

Reaction equation

HRID 597059 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[C:20]4[C:15](=[CH:16][C:17]([OH:21])=[CH:18][CH:19]=4)[C:14]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:13]3[CH3:28])=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.Cl[C:30](Cl)=[C:31](Cl)Cl.[CH3:35]N(C)C=O>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[C:20]4[C:15](=[CH:16][C:17]([O:21][CH2:35][CH2:30][CH3:31])=[CH:18][CH:19]=4)[C:14]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:13]3[CH3:28])=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 31373TetrachloroethyleneHCID 21449352Ethyl 1-(7-chloroquinazolin-4-yl)-5-hydroxy-2-methylindol-3-ylacetate

Product 1

HCID 21449327Ethyl 1-(7chloroquinazolin-4-yl)-2-methyl-5-n-propoxyindol-3-ylacetate

Procedure

A solution of ethyl 1-(7-chloroquinazolin-4-yl)-5-hydroxy-2-methylindol-3-ylacetate (1.0g.) in dry dimethyl-formamide (10ml.); dried by distillation from calcium hydride, and stored over sodium alumino-silicate) was added to sodium hydride (0.068g.), and the mixture was stirred under a slight vacuum (ca 150mm. Hg) at room temperature for 15 minutes. n-Propyl iodide (0.9g.) was added to the resulting clear solution, and the mixture stirred at room temperature overnight. The solution was added to water (300ml.) and extracted with ethyl acetate (3 × 40ml.). The combined extracts were washed with a saturated solution of sodium chloride (30ml.), dried (MgSO4), and then evaporated in vacuo. The yellow oil thus obtained was treated with tetrachloroethylene (100ml.) and the solution evaporated in vacuo. This process was then replaced with ethanol (50ml.) to give ethyl 1-(7chloroquinazolin-4-yl)-2-methyl-5-n-propoxyindol-3-ylacetate as a stiff yellow syrup [NMR: 2-CH3 at 7.65 τ; pure by TLC (systems A and D)].

Workup

  1. dry with materialdried by distillation from calcium hydride
  2. additionwas added to sodium hydride (0.068g.)
  3. additionn-Propyl iodide (0.9g.) was added to the resulting clear solution
  4. stirringthe mixture stirred at room temperature overnight
  5. additionThe solution was added to water (300ml.)
  6. extractionextracted with ethyl acetate (3 × 40ml.)
  7. washThe combined extracts were washed with a saturated solution of sodium chloride (30ml.)
  8. dry with materialdried (MgSO4)
  9. customevaporated in vacuo
  10. customThe yellow oil thus obtained
  11. customthe solution evaporated in vacuo

Sources & evidence

ORD record
ord-52b8c8b72f3746f799001bae010f2f45
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Linked notes

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