Acetic Anhydride → HCID 57312107, compound

HRID 439856Notes

Reaction equation

HRID 439856 reaction equation
[CH3:1][C:2]12[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C:10]1([CH3:18])[C:9]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:3]2.C(=O)(O)[O-].[Na+].[C:24](OC(=O)C)(=[O:26])[CH3:25]>>[C:24]([N:3]1[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=2[C@@:10]2([CH3:18])[CH2:11][C:12]3[C:17]([C@@:2]12[CH3:1])=[CH:16][CH:15]=[CH:14][CH:13]=3)(=[O:26])[CH3:25]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 22408488HCID 22408488, compound

Product 1

HCID 57312107HCID 57312107, compound

Procedure

4b,5,9b,10-tetrahydro-4b,9b-dimethylindeno[1,2-b]indole, (0.2 g, 0.85 mmol) was dissolved in acetic anhydride (1 cm3) and the solution stirred at room temperature for 16 hours. The reaction mixture was poured into saturated sodium bicarbonate solution and stirred for a further 1/2 hour. The mixture was then extracted with ether (3×15 cm3) and the combined organic extracts collected washed with brine, dried (Na2SO4) and evaporated to yield the title compound as an oil. This was purified by flash chromatography on silica gel eluting with 5-7% ethyl acetate/60°-80° petrol, to yield a colourless solid. Yield: 0.15 g, 64% .M.p. 81° C. 1H NMR (CDCl3) δ: 7.82 (1H, s), 6.99-7.29 (7H, m), 3.26 (1H, d, J=15.9 Hz), 2.97 (1H, d, J =15.9 Hz), 2.42 (3H, s), 1.77 (3H, s), 1.25 (3H, s).

Workup

  1. stirringstirred for a further 1/2 hour
  2. extractionThe mixture was then extracted with ether (3×15 cm3)
  3. customthe combined organic extracts collected
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-fa9d765230874f3ebc3d655ba0f51c68
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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