Dichloromethane → HCID 66834116, compound

HRID 61705Notes

Reaction equation

HRID 61705 reaction equation
ClCCl.[CH3:4][C:5]1([CH3:38])[C:17]2[NH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]#[N:19])[CH:14]=3)[C:9]=2[C:8](=[O:20])[C:7]2[CH:21]=[CH:22][C:23]([O:25][CH:26]3[CH2:31][O:30]C(C4C=CC=CC=4)[O:28][CH2:27]3)=[CH:24][C:6]1=2>O>[OH:30][CH2:31][CH:26]([CH2:27][OH:28])[O:25][C:23]1[CH:22]=[CH:21][C:7]2[C:8](=[O:20])[C:9]3[C:10]4[C:15](=[CH:14][C:13]([C:18]#[N:19])=[CH:12][CH:11]=4)[NH:16][C:17]=3[C:5]([CH3:4])([CH3:38])[C:6]=2[CH:24]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 668341506,6-Dimethyl-11-oxo-8-(2-phenyl-[1,3]dioxan-5-yloxy)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Product 1

HCID 66834116HCID 66834116, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Anhydrous ferric trichloride (56 mg, 5 eq.) was added to the dichloromethane (2 mL) suspension of 6,6-dimethyl-11-oxo-8-(2-phenyl-[1,3]dioxan-5-yloxy)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A7-13-1, 13 mg, 0.028 mmol), and stirred at room temperature for 1 hr. The reaction solution was added to water, and then extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by high performance liquid chromatography to obtain the title compound (7 mg, 46%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. customThe drying agent was removed by filtration
  5. customthe residues obtained
  6. concentrationafter concentration under reduced pressure
  7. customwere purified by high performance liquid chromatography

Sources & evidence

ORD record
ord-2565497d4db64e6d88715f50a92e8387
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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