Ethyl Acetate → 8-Methoxy-10,10-dimethyl-10H-11-oxa-2-aza-benzo[b]fluoren-5-one

HRID 61909Notes

Reaction equation

HRID 61909 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:18][C:17]3[C:16]4[CH:15]=[CH:14][N:13]=[CH:12][C:11]=4[O:10][C:9]=3[C:8]([CH3:20])([CH3:19])[C:7]=2[CH:21]=1.Cl([O-])=[O:23].[Na+].ON1C(=O)C2=CC=CC=C2C1=O.C(OCC)(=O)C>C(#N)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:18](=[O:23])[C:17]3[C:16]4[CH:15]=[CH:14][N:13]=[CH:12][C:11]=4[O:10][C:9]=3[C:8]([CH3:19])([CH3:20])[C:7]=2[CH:21]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10665N-HydroxyphthalimideHCID 23668197Sodium ChloriteHCID 66835135HCID 66835135, compound

Product 1

HCID 668347578-Methoxy-10,10-dimethyl-10H-11-oxa-2-aza-benzo[b]fluoren-5-oneYield 57.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

8-Methoxy-10,10-dimethyl-5,10-dihydro-11-oxa-2-aza-benzo[b]fluorene (Compound GT15-10, 20 mg) was dissolved in acetonitrile (0.2 ml) and water (0.15 ml), added with sodium chlorite (16 mg) and N-hydroxyphthalimide (2.3 mg), and the mixture was stirred at 40° C. for 40 min. To the reaction mixture, ethyl acetate was added. The organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine, and then concentrated under reduced pressure. The resulting residues were purified by silica gel column (ethyl acetate/hexane) to obtain the title compound (12 mg, 57%).

Workup

  1. washThe organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residues were purified by silica gel column (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e878285f2f684fac844263a4acb6385d
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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