Isopropanol → HCID 83528569, compound

HRID 1773310Notes

Reaction equation

HRID 1773310 reaction equation
C([N:9]1[CH2:18][C:17]2[CH:16]=[N:15][C:14]3[CH:19]=[C:20]([O:25][CH3:26])[C:21]([O:23][CH3:24])=[CH:22][C:13]=3[C:12]=2[CH2:11][CH2:10]1)(=O)C1C=CC=CC=1.O[Li].O.C(O)(C)C>CO.O>[CH3:26][O:25][C:20]1[C:21]([O:23][CH3:24])=[CH:22][C:13]2[C:12]3[CH2:11][CH2:10][NH:9][CH2:18][C:17]=3[CH:16]=[N:15][C:14]=2[CH:19]=1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 168937Lithium hydroxide, monohydrateHCID 118699729HCID 118699729, compound

Product 1

HCID 83528569HCID 83528569, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
64 °C

Procedure

A 2 L three-necked, round-bottomed flask, was equipped with a magnetic stirrer and stir bar, condenser, heating bath, thermocouple and nitrogen inlet. A stirred solution of 3-benzoyl-8,9-dimethoxy-1,2,3,4-tetrahydrobenzo[c]-2,7-naphthyridine (25.9 g, 74.4 mmol) and LiOH.H2O (34.4 g, 819 mmol) in methanol (800 mL) and water (55 mL) was heated at gentle reflux (internal temperature 62-66° C.) for 20 hours. Solvents were removed under reduced pressure and the residue was stirred in a mixture of methanol (180 mL) and dichloromethane (3 L) overnight. The batch was washed with saturated aqueous sodium chloride (0.5 L) diluted with water (0.4 L), and the separated organic layer was dried over anhydrous sodium sulfate (100 g). Removal of the drying agent by filtration and evaporation of solvent in vacuo gave a crude dark brown solid (12.1 g). The crude product was stirred in refluxing isopropanol (35 mL) for 1 hour, cooled to 22° C., and collected on a fritted glass funnel to afford the title compound as a grey solid (10.6 g, 58% yield).

Workup

  1. customA 2 L three-necked, round-bottomed flask, was equipped with a magnetic stirrer
  2. temperatureheating bath
  3. customSolvents were removed under reduced pressure
  4. stirringthe residue was stirred in a mixture of methanol (180 mL) and dichloromethane (3 L) overnight
  5. washThe batch was washed with saturated aqueous sodium chloride (0.5 L)
  6. additiondiluted with water (0.4 L)
  7. dry with materialthe separated organic layer was dried over anhydrous sodium sulfate (100 g)
  8. customRemoval of the drying agent
  9. filtrationby filtration and evaporation of solvent in vacuo
  10. customgave a crude dark brown solid (12.1 g)
  11. temperaturecooled to 22° C.
  12. customcollected on a fritted glass funnel

Sources & evidence

ORD record
ord-250d36b9cc614f38b1b5dd1777d52a39
Source dataset
uspto-grants-2016_02
Patent number
US09255096B1

Reaction notes

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