9-Oxofluorene-4-carboxylic acid → HCID 67360611, compound

HRID 2243333Notes

Reaction equation

HRID 2243333 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH-:9].[O:10]=[C:11]1[C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([C:24](O)=O)[C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2>C(O)(=O)C>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[N:9]=[C:24]([C:19]3[C:18]4[C:17]5[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=5)[C:11](=[O:10])[C:23]=4[CH:22]=[CH:21][CH:20]=3)[NH:1][C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 803619-Oxofluorene-4-carboxylic acidHCID 86621033HCID 86621033, compound

Product 1

HCID 67360611HCID 67360611, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3.0 g of (2-amino-4-chlorophenyl)amide of 9-oxo-9H-fluorene-4-carboxylic acid in 120 ml of glacial acetic acid is refluxed for 2.5 hours. Allow the mixture to return to room temperature and evaporate the reaction medium to dryness under vacuum. The residue is taken up with 75 ml of dichloromethane, and the organic phase is washed with twice 50 ml of a saturated solution of sodium bicarbonate, and 50 ml of a saturated solution of sodium chloride. After drying over magnesium sulphate, the organic phase is evaporated to dryness under vacuum. In this way, we obtain 3.12 g of 4-(6-chloro-1H-benzimidazol-2-yl)-9H-fluoren-9-one in the form of a beige foam with the following characteristics:

Workup

  1. temperatureis refluxed for 2.5 hours
  2. customto return to room temperature
  3. customevaporate the reaction medium to dryness under vacuum
  4. washthe organic phase is washed with twice 50 ml of a saturated solution of sodium bicarbonate, and 50 ml of a saturated solution of sodium chloride
  5. dry with materialAfter drying over magnesium sulphate
  6. customthe organic phase is evaporated to dryness under vacuum

Sources & evidence

ORD record
ord-4fe8279d4dc2419e8ff2aaebeb5afead
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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