9-Oxofluorene-4-carboxylic acid → HCID 59208194, compound

HRID 2243314Notes

Reaction equation

HRID 2243314 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH-:8].[O:9]=[C:10]1[C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([C:23](O)=O)[C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2>C(O)(=O)C>[NH:1]1[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N:8]=[C:23]1[C:18]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:9])[C:22]=2[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 803619-Oxofluorene-4-carboxylic acidHCID 86621027HCID 86621027, compound

Product 1

HCID 59208194HCID 59208194, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

In a 50-ml three-necked flask under an argon atmosphere, heat, at 80° C. for 2 hours, a solution of 3 g of the (2-amino-phenyl)amide of 9-oxo-9H-fluorene-4-carboxylic acid obtained in the preceding stage, in 150 ml of acetic acid. After cooling, the precipitate that formed is drained. After purification by silica gel flash chromatography, eluting with mixtures of dichloromethane and ethyl acetate (90-10 then 80-20 and finally 70-30 by volume), we obtain 1.73 g of 4-(1H-benzimidazol-2-yl)-fluoren-9-one in the form of a yellow powder, which is used as it is in the next stage, with the following characteristics:

Workup

  1. temperatureAfter cooling
  2. customthe precipitate that formed
  3. customAfter purification by silica gel flash chromatography
  4. washeluting with mixtures of dichloromethane and ethyl acetate (90-10

Sources & evidence

ORD record
ord-91000b449a9f4adba18f981a768e6866
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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