Acetic Acid → HCID 67361214, compound

HRID 2243371Notes

Reaction equation

HRID 2243371 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:11]=1[C:12]1[CH:13]=[CH:14][C:15]([Br:25])=[CH:16][C:17]=1[C:18]2=[N:23]O.C(O)C.C(O)(=O)C>O.[Zn]>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:11]=1[C:12]1[CH:13]=[CH:14][C:15]([Br:25])=[CH:16][C:17]=1[CH:18]2[NH2:23]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 702EthanolHCID 136385242HCID 136385242, compound

Product 1

HCID 67361214HCID 67361214, compoundYield 224%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

Place 500 mg of 5-(1H-benzimidazol-2-yl)-2-bromo -9H-fluoren-9-one oxime (Z,E) in suspension in a mixture of 3.5 ml of water, 7 ml of ethanol and 3.5 ml of acetic acid. Add 335 mg of powdered zinc and stir at room temperature for 19 hours. The insoluble residues are filtered over sintered glass and rinsed with ethanol. Evaporation of the solvent under reduced pressure is a colourless foam which is taken up in suspension in 100 ml of water. The pH of the supernatant is then brought to 9 by the addition of a 1N aqueous solution of sodium hydroxide, and the persisting precipitate is filtered off, and washed with 3 times 50 ml of water and twice 100 ml of isopropyl ether. After drying at 50° C. in an oven under vacuum, in this way we obtain 1.08 g of 5-(1H-benzimidazol-2-yl)-2-bromo-9H-fluorene-9(R,S)-amine, in the form of a white powder which is used as it is in the following stage.

Workup

  1. filtrationThe insoluble residues are filtered over sintered glass
  2. washrinsed with ethanol
  3. customEvaporation of the solvent under reduced pressure
  4. additionThe pH of the supernatant is then brought to 9 by the addition of a 1N aqueous solution of sodium hydroxide
  5. filtrationthe persisting precipitate is filtered off
  6. washwashed with 3 times 50 ml of water and twice 100 ml of isopropyl ether
  7. customAfter drying at 50° C. in an oven under vacuum, in this way we

Sources & evidence

ORD record
ord-a7ff719c759942c490dbae7cbc0cab67
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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