Methanol → HCID 19594690, compound

HRID 612607Notes

Reaction equation

HRID 612607 reaction equation
[CH2:1]([N:3]([CH2:28][CH3:29])[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:26][CH3:27])=[CH:11][C:12]([O:24][CH3:25])=[C:13]([N+:21]([O-])=O)[C:14]=1[C:15]2=[O:20])[CH3:2].C(=O)(O)[O-].[Na+].CO.C(Cl)[Cl:38]>C(O)C.O>[ClH:38].[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]([CH2:28][CH3:29])[CH2:1][CH3:2])[CH:19]=[CH:18][CH:17]=3)[C:9]=2[C:10]([O:26][CH3:27])=[CH:11][C:12]=1[O:24][CH3:25]

Participants

7

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 11036795HCID 11036795, compound

Product 1

HCID 19594690HCID 19594690, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Prepare a mixture of 5-(2-diethylamino-ethoxy)-2,4-dimethoxy-1-nitro-fluoren-9-one (0.08 g, 0.18 mmole) and stannous chloride dihydrate (SnCl2.2H2O, 0.80 g, 3.5 mmole) in 20 mL ethanol. Heat at 70° C. under argon overnight. Dilute with about 60 mL water and make slightly basic by addition of 5% sodium bicarbonate. Extract the precipitate with ethyl acetate and dry over magnesium sulfate. Filter and evaporate the solvent. Make acidic (to pH=2) with 5% hydrochloric acid and extract the organics. Make the aqueous phase basic (to pH=8) and extract with methylene chloride. Dry over magnesium sulfate. Filter and evaporate the solvent to obtain a red oil. Chromatron with 7% methanol in methylene choride and condense under high vacuum to obtain the free base of the title compound (0.48 g). m.p. 208°-210° C.

Workup

  1. customPrepare
  2. extractionExtract the precipitate with ethyl acetate
  3. dry with materialdry over magnesium sulfate
  4. filtrationFilter
  5. customevaporate the solvent
  6. extractionextract the organics
  7. extractionextract with methylene chloride
  8. dry with materialDry over magnesium sulfate
  9. filtrationFilter
  10. customevaporate the solvent
  11. customto obtain a red oil

Sources & evidence

ORD record
ord-09f27f7be92a4133bbd832c4bca3c8a6
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

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