Acetic Acid → HCID 15082727, compound

HRID 439860Notes

Reaction equation

HRID 439860 reaction equation
[CH:1]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:2]=1[CH2:3][C:4]1[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][C:5]=12.C([BH3-])#N.[Na+].[C:21](O)(=O)[CH3:22]>>[CH2:21]([N:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[C@H:4]2[CH2:3][C:2]3[C:13]([C@@H:5]12)=[CH:14][CH:15]=[CH:16][CH:1]=3)[CH3:22]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 975985,10-Dihydroindeno[1,2-b]indoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 15082727HCID 15082727, compound

Procedure

5,10-Dihydroindeno[1,2-b]indole (60.0 g, 0.29M) was vigorously stirred in glacial acetic acid (1000 cm3) and to it was added sodium cyanoborohydride (79 g, 1.25M) portion-wise over 40 minutes. After 3 hours stirring the reaction mixture was poured onto ice-water (2000 cm3) and the gelatinous solid which formed was separated and stirred with a mixture of ethyl acetate (75 cm3) and water (100 cm3). A colourless solid remained this was found to be unreacted starting material (19.0 g). The original filtrate was extracted with ethyl acetate (2×75 cm3) and the combined organic phases dried and evaporated. The residue was then partly dissolved in a mixture of 60°-80° C. petroleum ether (20 cm3) and ethyl acetate (40 cm3). The residual solid was removed and shown to be impure starting material (2.5 g). The filtrate was extracted with 2M hydrochloric acid (8×25 cm3) and the combined acid extracts were washed with ethyl acetate (2×15 cm3), prior to basification with 0.89 ammonia. The oil which separated was extracted into ethyl acetate (6×25 cm3) and the combined organic layers were then dried and evaporated to give the title compound as a colourless oil. Yield: 34 g, 75%. 1H NMR (CDCl3) δ: 1.20 (3H, t, J=7.0 Hz), 3.05 (1H, dd, J=16.5 and 5.0 Hz), 3.38 (2H, q, J=7.0 Hz), 3.40 (1, dd, J=16.5 and 9.0 Hz), 4.12 (1H, ddd, J=9.0, 5.0 and 5.0 Hz), 5.11 (1H, d, J=9.0 Hz), 6.33 (1H, d, J=7.0 Hz), 6.57 (1H, dt, J=7.5 and 1.0 Hz), 7.02 (1H, t, J=8.0 Hz ), 7.08 (1H, d, J=8.0 Hz), 7.14-7.20 (3H, m), 7.34-7.40 (1H, m).

Workup

  1. additionwas poured onto ice-water (2000 cm3)
  2. customthe gelatinous solid which formed
  3. customwas separated
  4. stirringstirred with a mixture of ethyl acetate (75 cm3) and water (100 cm3)
  5. extractionThe original filtrate was extracted with ethyl acetate (2×75 cm3)
  6. customthe combined organic phases dried
  7. customevaporated
  8. dissolutionThe residue was then partly dissolved in a mixture of 60°-80° C. petroleum ether (20 cm3) and ethyl acetate (40 cm3)
  9. customThe residual solid was removed
  10. extractionThe filtrate was extracted with 2M hydrochloric acid (8×25 cm3)
  11. washthe combined acid extracts were washed with ethyl acetate (2×15 cm3)
  12. customThe oil which separated
  13. extractionwas extracted into ethyl acetate (6×25 cm3)
  14. customthe combined organic layers were then dried
  15. customevaporated

Sources & evidence

ORD record
ord-e3220c47b67c45468fa8eb342521b23a
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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