7-Nitro-9-oxo-4-fluorenecarboxylic acid → 5-(1H-benzimidazol-2-yl)-2-nitro-9H-fluoren-9-one
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH-:8].[N+:9]([C:12]1[CH:24]=[C:23]2[C:15]([C:16]3[C:17]([C:26](O)=O)=[CH:18][CH:19]=[CH:20][C:21]=3[C:22]2=[O:25])=[CH:14][CH:13]=1)([O-:11])=[O:10]>C(O)(=O)C>[NH:1]1[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N:8]=[C:26]1[C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:16]=1[C:15]1[CH:14]=[CH:13][C:12]([N+:9]([O-:11])=[O:10])=[CH:24][C:23]=1[C:22]2=[O:25]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
The procedure used in Example 68 is followed. In a 100 ml round-bottomed flask under an argon atmosphere, heat, at 130° C. for 4 hours, a suspension of 1.6 g of (2-aminophenyl)amide of 7-nitro-9-oxo-9H -fluorene-4-carboxylic acid, obtained in the previous stage, in 30 ml of acetic acid. After cooling, the insoluble material that formed is filtered off, and washed successively with water, with a saturated aqueous solution of sodium hydrogen carbonate and then with water. After purification by flash chromatography on silica gel (40-63 μm), eluting with a mixture of dichloromethane and 7N ammoniacal methanol (9/1 by volume), then formation of a paste in diisopropyl ether, in this way we obtain 550 mg of 5-(1H-benzimidazol-2-yl)-2-nitro-9H-fluoren-9-one, in the form of a yellow powder, which is used as it is in the following stage, with the following characteristics:
Workup
- temperatureAfter cooling
- customthe insoluble material that formed
- filtrationis filtered off
- washwashed successively with water, with a saturated aqueous solution of sodium hydrogen carbonate
- customAfter purification by flash chromatography on silica gel (40-63 μm)
- washeluting with a mixture of dichloromethane and 7N ammoniacal methanol (9/1 by volume)
Sources & evidence
- ORD record
- ord-1d82322b3d044f08bdfd777331fa8416
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07674795B2
Reaction notes
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