Ethanol → HCID 67359644, compound

HRID 2243338Notes

Reaction equation

HRID 2243338 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10]3[C:22]4[C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[C:15](=[N:23]O)[C:14]=4[CH:13]=[CH:12][CH:11]=3)[NH:7][C:6]=2[CH:25]=1.C(O)C.O>C(O)(=O)C.[Zn]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10]3[C:22]4[C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[CH:15]([NH2:23])[C:14]=4[CH:13]=[CH:12][CH:11]=3)[NH:7][C:6]=2[CH:25]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 962WaterHCID 136360172HCID 136360172, compound

Product 1

HCID 67359644HCID 67359644, compoundYield 18.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

Stir, at ambient temperature, a mixture of 390 mg of 4-(6-bromo-1H-benzimidazol-2-yl)-9H-fluoren-9-one oxime (Z, E) in a mixture of 2 ml of acetic acid, 2 ml of ethanol and 2 ml of water in the presence of 65 mg of powdered zinc. After half an hour, add a further 65 mg of powdered zinc and maintain the stirring for approximately 3 hours. Add Celite, filter over sintered glass and wash the precipitate with 200 ml of a mixture of methanol and dichloromethane (20/80 by volume). Evaporate the filtrate to dryness under vacuum, add twice 50 ml of toluene and, each time, re-evaporate to dryness under vacuum. The residue is chromatographed on silica gel, eluting with a mixture of dichloromethane and a 7N solution of ammonia in methanol (90/10 by volume). In this way, we obtain 69 mg of 4-(6-bromo-1H-benzimidazol-2-yl)-9H-fluoren-9(R,S)-amine, in the form of a beige foam with the following characteristics:

Workup

  1. waitAfter half an hour
  2. temperaturemaintain the stirring for approximately 3 hours
  3. filtrationAdd Celite, filter over sintered glass
  4. washwash the precipitate with 200 ml of a mixture of methanol and dichloromethane (20/80 by volume)
  5. customEvaporate the filtrate to dryness under vacuum
  6. additionadd twice 50 ml of toluene
  7. customeach time, re-evaporate to dryness under vacuum
  8. customThe residue is chromatographed on silica gel
  9. washeluting with a mixture of dichloromethane

Sources & evidence

ORD record
ord-d8bc47f70c69405d81fef5ddde41a583
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

Loading…