HCID 70625650, compound → HCID 85889757, compound

HRID 1763898Notes

Reaction equation

HRID 1763898 reaction equation
[CH3:1][N:2]1[CH:11]([CH3:12])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(O)[C:9]2[C:4](=[CH:5][C:6]([O:20][CH3:21])=[CH:7][CH:8]=2)[CH2:3]1>Cl>[CH3:1][N:2]1[CH:11]([CH3:12])[CH:10]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:9]2[C:4](=[CH:5][C:6]([O:20][CH3:21])=[CH:7][CH:8]=2)[CH2:3]1

Participants

3

Reactant 1

HCID 70625650HCID 70625650, compound

Product 1

HCID 85889757HCID 85889757, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Saturated ethanolic hydrogen chloride (800 ml) was added to (7) (21 g) and the solution was refluxed for 2 hr. and left to stand at room temperature for 16 hr. Ethanol was removed under reduced pressure, the residue was taken up in methanol and sodium borohydride (30 g) added portion-wise. Methanol was removed under reduced pressure and the residue taken up in water and ether. The aqueous layer was extracted with ether and the combined ether layers extracted with dilute sulphuric acid(2N). The acid layers were basified and extracted with ether. The combined ether layers were dried (MgSO4). Removal of the solvent under reduced pressure gave the title compound as an oil.

Workup

  1. temperaturethe solution was refluxed for 2 hr
  2. waitand left
  3. customEthanol was removed under reduced pressure
  4. additionsodium borohydride (30 g) added portion-wise
  5. customMethanol was removed under reduced pressure
  6. extractionThe aqueous layer was extracted with ether
  7. extractionthe combined ether layers extracted with dilute sulphuric acid(2N)
  8. extractionextracted with ether
  9. dry with materialThe combined ether layers were dried (MgSO4)
  10. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-63a439350ddb44d99c7a91d6cfa84e56
Source dataset
uspto-grants-1978_09
Patent number
US04113869

Reaction notes

Loading…