Benzosuberone → HCID 2826075, compound

HRID 2383401Notes

Reaction equation

HRID 2383401 reaction equation
[CH:1]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11](=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1.CO[CH:15](OC)[N:16]([CH3:18])[CH3:17]>>[CH3:15][N:16](/[CH:18]=[C:10]1/[C:11](=[O:12])[C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:6]=2[CH2:7][CH2:8][CH2:9]/1)[CH3:17]

Participants

3

Reactant 2

HCID 70003BenzosuberoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 2826075HCID 2826075, compoundYield 82%

Procedure

A solution of 6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (1.0 g, 6.24 mmol) in 1,1-dimethoxy-N,N-dimethylmethanamine (2.5 mL) was heated at 100° C. for 24 hours. On completion of the reaction, the solvent was removed under reduced pressure. The oily residue was triturated with n-hexane (2×50 mL) to give the desired pure product, (E)-6-((dimethylamino)methylene)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (1.1 g, 82%) as a brown solid. 1H NMR (CDCl3, 400 MHz): δ 7.75 (s, 1H), 7.62 (d, J=6.2 Hz, 1H), 7.34-7.25 (m, 2H), 7.09 (d, J=6.4 Hz, 1H), 3.11 (s, 6H), 2.75 (t, J=6.8 Hz, 2H), 2.35 (t, J=6.4 Hz, 2H), 1.83 (quintet, J=6.8 Hz, 2H). LCMS [M+H]: 216.

Workup

  1. customOn completion of the reaction
  2. customthe solvent was removed under reduced pressure
  3. customThe oily residue was triturated with n-hexane (2×50 mL)

Sources & evidence

ORD record
ord-d292f8ee6feb4262b6e04f6f9cb72f17
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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