Hydrochloric Acid → HCID 14279565, compound

HRID 622747Notes

Reaction equation

HRID 622747 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]#[N:13])=[CH:7][CH:6]=1.[O:14]([C:21]1[N:26]=[C:25]([CH2:27][CH2:28][C:29](OC)=[O:30])[CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>O1CCCC1>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:29](=[O:30])[CH2:28][CH2:27][C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([O:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:26]=2)[C:12]#[N:13])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 66031Benzeneacetonitrile, 4-methoxy-HCID 14279564HCID 14279564, compound

Product 1

HCID 14279565HCID 14279565, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, 235 mg of sodium hydride (60% oil dispersion) were added to 50 ml of dry tetrahydrofuran, and the mixture was heated to 50° C. to 60° C. A solution of 864 mg of 4-methoxyphenylacetonitrile and 1.51 g of methyl 3-(6-phenoxypyridin-2-yl)propionate in 10 ml of dry tetrahydrofuran were added dropwise thereto over 5 minutes. After dropwise addition, the reaction solution was heated under reflux for 2 hours, cooled with ice, poured into ice water, neutralized to a pH of 7 with aqueous dilute hydrochloric acid and extracted twice with ethyl acetate. The ethyl acetate layers were combined and dried over anhydrous magnesium sulfate, and the solvent was removed by evaporation under reduced pressure. The residue crystallized, so that the crystal was washed with a little diethyl ether, filtered and dried to obtain 0.91 g of the desired 2-(4-methoxyphenyl)-3-oxo-5-(6-phenoxypyridin-2-yl)valeronitrile [corresponding to the compound represented by the foregoing general formula (X) wherein R1 is a methoxy group, R2, R5 and R6 are a hydrogen atom] as a crystal.

Workup

  1. temperaturethe mixture was heated to 50° C. to 60° C
  2. additionAfter dropwise addition
  3. temperaturethe reaction solution was heated
  4. temperatureunder reflux for 2 hours
  5. temperaturecooled with ice
  6. extractionextracted twice with ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed by evaporation under reduced pressure
  9. customThe residue crystallized, so that the crystal
  10. washwas washed with a little diethyl ether
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-3ff02ad432f849eaa8c737251f127303
Source dataset
uspto-grants-1988_09
Patent number
US04772633

Reaction notes

Loading…