9-Oxofluorene-4-carboxylic acid → HCID 67359009, compound

HRID 2243324Notes

Reaction equation

HRID 2243324 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[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-])O.[Na+]>C(O)(=O)C.O>[CH3:8][C:4]1[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]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 803619-Oxofluorene-4-carboxylic acidHCID 516892Sodium BicarbonateHCID 86621029(2-Amino-6-methylphenyl)amide

Product 1

HCID 67359009HCID 67359009, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The procedure used in Example 68 is followed. In a 250 ml round-bottomed flask under an argon atmosphere, reflux, for 6 hours, a suspension of 5 g of (2-amino-6-methylphenyl)amide of 9-oxo-9H-fluorene-4-carboxylic acid, obtained in the previous stage, in 100 ml of acetic acid. After cooling, bring to dryness under reduced pressure. Take the residue up in 25 ml of water then bring to pH=8 by addition of a saturated aqueous solution of sodium hydrogen carbonate. The precipitate that formed is filtered off, washed with water, and made into a paste with diisopropyl ether, and in this way, we obtain 4.7 g of 4-(4-methyl-1H-benzimidazol-2-yl)-9H-fluoren-9-one, in the form of an orange powder, which is used as it is in the following stage, with the following characteristics:

Workup

  1. temperatureIn a 250 ml round-bottomed flask under an argon atmosphere, reflux, for 6 hours
  2. temperatureAfter cooling
  3. customThe precipitate that formed
  4. filtrationis filtered off
  5. washwashed with water

Sources & evidence

ORD record
ord-dddcc537beb54a5384c268608f75438e
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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