Ethanol → HCID 67360306, compound

HRID 2243335Notes

Reaction equation

HRID 2243335 reaction equation
[Cl: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]>[Cl: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 136360171HCID 136360171, compound

Product 1

HCID 67360306HCID 67360306, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

Stir, at room temperature, a mixture of 345 mg of 4-(6-chloro-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 1 hour and 3 hours, add, each time, a further 65 mg of powdered zinc and maintain the stirring for approximately 4 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). The filtrate is evaporated to dryness under vacuum, add twice 50 ml of toluene and re-evaporate, each time, to dryness under vacuum. The residue is chromatographed on silica gel, eluting with a mixture of dichloromethane-7N solution of ammonia in methanol (90/10 by volume). In this way, we obtain 275 mg of 4-(6-chloro-1H-benzimidazol-2-yl)-9H-fluorene-9(R,S)-amine in the form of a beige foam with the following characteristics:

Workup

  1. addition3 hours, add
  2. filtrationAdd Celite, filter over sintered glass
  3. washwash the precipitate with 200 ml of a mixture of methanol and dichloromethane (20/80 by volume)
  4. customThe filtrate is evaporated to dryness under vacuum
  5. additionadd twice 50 ml of toluene
  6. customre-evaporate
  7. customThe residue is chromatographed on silica gel
  8. washeluting with a mixture of dichloromethane-7N solution of ammonia in methanol (90/10 by volume)

Sources & evidence

ORD record
ord-402cf70b5d494871bda23e338eea42e5
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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