Acetone → HCID 55263195, compound

HRID 1751961Notes

Reaction equation

HRID 1751961 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[CH2:8][CH2:9][C:10]3(OCC[O:14]3)[CH2:11][C:12]=2[CH:13]=1)([O-:3])=[O:2].CC(C)=O.Cl.C([O-])(O)=O.[Na+]>O>[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[CH2:8][CH2:9][C:10](=[O:14])[CH2:11][C:12]=2[CH:13]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59138781HCID 59138781, compound

Product 1

HCID 55263195HCID 55263195, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

The title compound was prepared according to the procedure of Pelcman (W02006032851, 1996). A 250 mL flask, equipped with a magnetic stirbar and reflux condenser, was charged with 3′-nitro-7′,8′-dihydro-5′H-spiro[1,3-dioxolane-2,6′-quinoline] (4.75 g, 20.1 mmol), acetone (65 mL), hydrochloric acid (2N (aq), 42 mL), and water (21 mL). The mixture was heated to 65° C. for 1 h, then to 80° C. for 30 minutes. The mixture was cooled to ambient temperature and neutralized with saturated NaHCO3 (aq) until pH=8. The mixture was extracted with EtOAc (3×) and the combined organic portions were dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (30 to 60% EtOAc in hexanes) to afford the title compound (2.5 g, 65%).

Workup

  1. customThe title compound was prepared
  2. customA 250 mL flask, equipped with a magnetic stirbar
  3. temperaturereflux condenser
  4. extractionThe mixture was extracted with EtOAc (3×)
  5. dry with materialthe combined organic portions were dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (30 to 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a46dbe50840b45f4be8d996390f1d57f
Source dataset
uspto-grants-2015_10
Patent number
US09162983B2

Reaction notes

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