Hydrochloric Acid → HCID 22861098, compound

HRID 439849Notes

Reaction equation

HRID 439849 reaction equation
[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[CH:10][C:9]2[NH:8][C:7]3[C:13]4[C:18]([CH2:19][C:6]=3[C:5]=2[C:4]=1[CH3:20])=[CH:17][CH:16]=[CH:15][CH:14]=4.O1CCN(B)CC1.Cl.[OH-].[Na+]>O1CCOCC1>[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[CH:10][C:9]2[NH:8][C@@H:7]3[C:13]4[C:18]([CH2:19][C@@H:6]3[C:5]=2[C:4]=1[CH3:20])=[CH:17][CH:16]=[CH:15][CH:14]=4

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 5028646HCID 5028646, compoundHCID 22408528HCID 22408528, compound

Product 1

HCID 22861098HCID 22861098, compoundYield 917%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To an solution of 0.8 g (0.3 mmol) of 5,10-dihydro-8-methoxy-7,9-dimethylindeno[1,2-b]indole and 1,21 g of morpholino borane in 4 ml of dioxane was added dropwise 1 ml of conc. hydrochloric acid. The mixture was refluxed for 30 minutes, then cooled whereupon 3 ml of 6M hydrochloric acid was added. The resulting mixture was then refluxed for 15 minutes. After cooling the solution was alkalinized with aqueous sodium hydroxide and extracted three times with ether. Drying (MgSO4) and evaporation gave a crude product, which was crystallized by dissolving in ethyl acetate and addition of light petroleum at -20° C. Filtration gave 0.73 g (92%) of the title compound. 1H NMR(CDCl3) 2.08 (3H,s), 3.15-3.25 (1H,dd), 3,42-3,55 (1H,dd), 3.7 (3H,s), 4.1-4.22 (1H,t) 5.22-5.28 (1H,d), 6.42-6.46 (1H,d), 6.6- 6.65 (1H,d) 7.14-7.25 (3H,m), 7.3-7.4 (1H,m).

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. additionwas added
  3. temperatureThe resulting mixture was then refluxed for 15 minutes
  4. temperatureAfter cooling the solution
  5. extractionextracted three times with ether
  6. customDrying
  7. custom(MgSO4) and evaporation
  8. customgave a crude product, which
  9. customwas crystallized
  10. dissolutionby dissolving in ethyl acetate
  11. additionaddition of light petroleum at -20° C
  12. filtrationFiltration

Sources & evidence

ORD record
ord-f4d44185409646448af7573fe68793ef
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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