N-Hydroxyphthalimide → 8-Methoxy-10,10-dimethyl-10H-11-oxa-4-aza-benzo[b]fluoren-5-one

HRID 2275281Notes

Reaction equation

HRID 2275281 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:18][C:17]3[C:16]4[N:15]=[CH:14][CH: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>CC#N.O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:18](=[O:23])[C:17]3[C:16]4[N:15]=[CH:14][CH: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 3

HCID 10665N-HydroxyphthalimideHCID 23668197Sodium ChloriteHCID 66835156HCID 66835156, compound

Product 1

HCID 668342278-Methoxy-10,10-dimethyl-10H-11-oxa-4-aza-benzo[b]fluoren-5-oneYield 70%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

8-Methoxy-10,10-dimethyl-5,10-dihydro-11-oxa-4-aza-benzo[b]fluorene (Compound GT15-3, 22 mg) was dissolved in MeCN (0.26 ml) and water (0.13 ml), added with sodium chlorite (14 mg) and N-hydroxyphthalimide (2.6 mg), and the mixture was stirred at 40° C. for 1 hr. The reaction mixture was diluted with ethyl acetate. 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 (16 mg, 70%).

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-6ed79731168747fd9f29b5cecf8ec827
Source dataset
uspto-grants-2015_09
Patent number
US09126931B2

Reaction notes

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