3-Hydrazinylbenzonitrile → 9-Bromo-8-methoxy-6,6-dimethyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61781Notes

Reaction equation

HRID 61781 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8]([CH3:15])([CH3:14])[C:7](=O)[CH2:6][CH2:5]2.[NH:17]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[C:22]#[N:23])N>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:9]2[C:8]([CH3:15])([CH3:14])[C:7]3[NH:17][C:19]4[C:26]([C:6]=3[CH2:5][C:4]=2[CH:3]=1)=[CH:25][CH:24]=[C:21]([C:22]#[N:23])[CH:20]=4

Participants

4

Reactant 2

HCID 14881453-HydrazinylbenzonitrileHCID 545785436-Bromo-7-methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-one2×

Product 1

HCID 668341279-Bromo-8-methoxy-6,6-dimethyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
100 °C

Procedure

6-Bromo-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound E1, 7.89 g, 27.85 mmol) and 3-hydrazino-benzonitrile (4.45 g, 1.2 eq.) were dissolved in TFA (250 mL), and stirred at 100° C. for 2 hr. TFA was removed under reduced pressure and the residues were added with saturated aqueous solution of NaHCO3 (500 mL), followed by extraction 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 added with ethyl acetate. After stirring at room temperature, the precipitated solid was separated by filtration (Compound E2-2). The filtrate was concentrated under reduced pressure to obtain the title compound as a mixture with E2-2 (yellowish white powder, 2.65 g).

Workup

  1. customTFA was removed under reduced pressure
  2. additionthe residues were added with saturated aqueous solution of NaHCO3 (500 mL)
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customThe drying agent was removed by filtration
  7. customthe residues obtained
  8. concentrationafter concentration under reduced pressure
  9. additionwere added with ethyl acetate
  10. stirringAfter stirring at room temperature
  11. customthe precipitated solid was separated by filtration (Compound E2-2)
  12. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4c3e70ac923f40d398a147852c75c47a
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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