HCID 19780362, compound → HCID 19780349, compound

HRID 2081688Notes

Reaction equation

HRID 2081688 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:18](=[CH:19][CH:20]=1)[C:10]1[NH:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:9]=1[CH2:8]2)(=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:18](=[CH:19][CH:20]=1)[C:10]1[NH:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:9]=1[CH2:8]2)[CH3:2]

Participants

4

Reactant 2

HCID 19780362HCID 19780362, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19780349HCID 19780349, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5,10-dihydro-2-(N-acetylamino)indeno[1,2,b]-indole (0.70 g, 2.8 mM) in dry tetrahydrofuran (50 cm3), under a protective atmosphere of nitrogen, was treated with lithium aluminium hydride (0.40 g, 10.50 mM) during the course of 3 hours. The mixture was then heated to reflux for a further 3 hours, and eventually cooled. Excess reagent was destroyed by the addition of a saturated solution of sodium potassium tartrate (5 cm3) and the organic phase separated. The residual aqueous slurry was extracted with tetrahydrofuran (3×10 cm3) and the extracts and organic phase were combined, filtered through phase transfer paper, and evaporated. This gave the title compound as a pale yellow solid. M.p. 225° C. Yield; 0.47 g, 71%. 1H NMR (CDCl3) δ: 1.23 (3H, t, J=7.0 Hz), 3.09 (2H, q, J=7.0Hz), 3.59 (2H, s), 4.80 (1 H, br.s), 6.56 (1H, d, J=7.5Hz), 6.87 (1H, s), 7.01 (2H, br.m), 7.32-7.48 (3H, br.m), 10.47 (1H, br.s).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for a further 3 hours
  3. temperatureeventually cooled
  4. customExcess reagent was destroyed by the addition of a saturated solution of sodium potassium tartrate (5 cm3)
  5. customthe organic phase separated
  6. extractionThe residual aqueous slurry was extracted with tetrahydrofuran (3×10 cm3)
  7. filtrationfiltered through phase transfer paper
  8. customevaporated

Sources & evidence

ORD record
ord-bd387fb5b6154d418f52b92f9ea43969
Source dataset
uspto-grants-1993_02
Patent number
US05185360

Reaction notes

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