Hydrochloric Acid → HCID 22338307, compound

HRID 1816463Notes

Reaction equation

HRID 1816463 reaction equation
O[CH:2]=[C:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:12][CH3:13])[CH:9]=2)[C:4]1=O.Cl.[NH2:16][CH:17]([CH3:21])[CH2:18][NH:19][NH2:20].C([O-])(O)=O.[Na+]>C(O)C.CO>[CH3:13][O:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[C:4]1[N:19]([CH2:18][CH:17]([NH2:16])[CH3:21])[N:20]=[CH:2][C:3]=1[CH2:11]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 13183609(2-Aminopropyl)hydrazineHCID 697542672-Hydroxymethylene-5-methoxy-1-indanone

Product 1

HCID 22338307HCID 22338307, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 887MethanolSolvent

Procedure

To a solution of the product from Step A (1.9 g, 10 mmol) in ethanol (20 mL) was added a 1 N solution of HCl in a 1:1 mixture of methanol and ethanol followed by 2-aminopropylhydrazine (0.9 g, 10 mmol) and the solution was heated to reflux for 16 h. The solution was allowed to cool, poured into aqueous NaHCO3, extracted with ethyl acetate (2×20 mL), dried (Na2SO4) and concentrated. The crude material was taken up in 0.1 N HCl and washed with ether (2×20 mL), basified by the addition of NaHCO3 and extracted with ethyl acetate (2×20 mL). The combined organic extracts were dried (Na2SO4) and concentrated to a residue, which was purified by chromatography (silica, 10% methanol in dichloromethane) to furnish an oil (0.48 g, 20%); MS m/z 244 [M+H]+.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 16 h
  3. temperatureto cool
  4. extractionextracted with ethyl acetate (2×20 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. washwashed with ether (2×20 mL)
  8. additionbasified by the addition of NaHCO3
  9. extractionextracted with ethyl acetate (2×20 mL)
  10. dry with materialThe combined organic extracts were dried (Na2SO4)
  11. concentrationconcentrated to a residue, which
  12. customwas purified by chromatography (silica, 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-3fc14f8971bf4504ba0b4552e01e2109
Source dataset
uspto-grants-2005_04
Patent number
US06884816B2

Reaction notes

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