Diethyl Ether → Ethyl 1-quinazolin-4-ylindol-3-ylacetate

HRID 597040Notes

Reaction equation

HRID 597040 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:12]2)=[N:3][CH:2]=1.C(OCC)C>[Pd].C1(OC2C=CC=CC=2)C=CC=CC=1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:12]2)=[N:3][CH:2]=1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 54457736Ethyl 1-quinazolin-4-ylindolin-3-ylacetate

Product 1

HCID 21449394Ethyl 1-quinazolin-4-ylindol-3-ylacetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7583Diphenyl EtherSolvent

Procedure

A mixture of ethyl 1-quinazolin-4-ylindolin-3-yl-acetate (2.6g.) and 10% w/w palladium on charcoal catalyst (1.3g.) in diphenyl ether (20ml.) was heated under reflux for 30 minutes. The mixture was cooled to room temperature, mixed with diethyl ether (50ml.) and filtered through diatomaceous earth. The solid residue was washed with diethyl ether (50ml.). The combined diethyl ether solution was evaporated in vacuo, and the residue was chromatographed on silica gel (ca 150g.) using, as eluant, petroleum ether (b.p. 40°-60° C.) containing an increasing proportion of diethyl ether. Diphenyl ether was recovered from the first fractions (rich in petroleum ether). Evaporation in vacuo of later fractions gave a syrup which crystallised from a mixture of diethyl ether and petroleum ether (b.p. 40°-60° C.) to give ethyl 1-quinazolin-4-ylindol-3-ylacetate, m.p. 65°-67° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. filtrationfiltered through diatomaceous earth
  4. washThe solid residue was washed with diethyl ether (50ml.)
  5. customThe combined diethyl ether solution was evaporated in vacuo
  6. customthe residue was chromatographed on silica gel (ca 150g.)
  7. additionpetroleum ether (b.p. 40°-60° C.) containing an increasing proportion of diethyl ether
  8. customDiphenyl ether was recovered from the first fractions (rich in petroleum ether)
  9. customEvaporation in vacuo of later fractions
  10. customgave a syrup which
  11. customcrystallised from a mixture of diethyl ether and petroleum ether (b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-9b3c1d080fc64c2194dfd807913febf8
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Reaction notes

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