Water → HCID 9822211, compound

HRID 612608Notes

Reaction equation

HRID 612608 reaction equation
[CH2:1]([N:3]([CH2:30][CH3:31])[CH2:4][CH2:5][O:6][C:7]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:8]=1[C:9]1[C:10]([O:28][CH3:29])=[CH:11][C:12]([O:24][CH2:25][CH2:26][CH3:27])=[C:13]([N+:21]([O-])=O)[C:14]=1[C:15]2=[O:20])[CH3:2].O.C(=O)(O)[O-].[Na+]>C(O)C.C(OCC)C>[NH2:21][C:13]1[C:14]2[C:15](=[O:20])[C:16]3[C:8](=[C:7]([O:6][CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:30][CH3:31])[CH:19]=[CH:18][CH:17]=3)[C:9]=2[C:10]([O:28][CH3:29])=[CH:11][C:12]=1[O:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 19594819HCID 19594819, compound

Product 1

HCID 9822211HCID 9822211, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Prepare a solution, under argon, of 5-(2-diethylamino-ethoxy)-4-methoxy-1-nitro-2-propoxy-fluoren-9-one (0.52 g, 1.2 mmole) and stannous chloride (SnCl2, 1.3 g, 6 mmole) in 60 mL ethanol. Reflux overnight. Reduce volume on a rotovap. Add 200 mL deionized water and make basic with sodium bicarbonate. Extract with methylene chloride. Dry the organic layer with magnesium sulfate. Filter and evaporate on a rotary evaporator to give a red oil. Take up in anhydrous diethyl ether and filter through celite. Precipitate the hydrochloride salt by adding ethereal HCl. Filter the resulting red solid and wash with diethyl ether. Place under a high vacuum overnight at 100° C. to give the purified hydrochloride salt of the title compound. m.p. 163-165° C. Yield 0.338 g, 70%. Rf =0.33; 5% methanol/CH2Cl2.

Workup

  1. customPrepare a solution
  2. temperatureReflux overnight
  3. additionAdd 200 mL
  4. extractionExtract with methylene chloride
  5. dry with materialDry the organic layer with magnesium sulfate
  6. filtrationFilter
  7. customevaporate on a rotary evaporator
  8. customto give a red oil
  9. filtrationfilter through celite
  10. customPrecipitate the hydrochloride salt
  11. additionby adding ethereal HCl
  12. filtrationFilter the resulting red solid
  13. washwash with diethyl ether
  14. customPlace under a high vacuum overnight at 100° C.

Sources & evidence

ORD record
ord-9d9e5bc95a054da8bd60eba252f8cad9
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

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