4-Nitrophenol → HCID 10256405, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:14]=1[N:13]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:12]1[C:11]([O:23][CH3:24])=[CH:10][CH:9]=[C:8]([C:25](O)=[O:26])[C:7]2=1.S(Cl)([Cl:30])=O.[CH3:32][N:33]([CH:35]=O)C.[N+:37]([C:40]1[CH:45]=CC(O)=CC=1)([O-])=O.[CH:47]([Cl:50])(Cl)Cl>>[Cl:30][C:45]1[CH:32]=[N:33][CH:35]=[C:47]([Cl:50])[C:40]=1[NH:37][C:25]([C:8]1[C:7]2[C:6]3[C:14](=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=3)[N:13]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[C:12]=2[C:11]([O:23][CH3:24])=[CH:10][CH:9]=1)=[O:26]Participants
6
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 8-chloro-9-(4-Fluorobenzyl)-1-methoxy-9H-4-carbazole carboxylic acid (130 mg, 0.327 mmoles) in 10 mL dry chloroform, thionyl chloride (0.071 mL, 0.981 mmoles) was added followed by a drop of DMF. The reaction mixture was stirred for 1 hr at 25° C. under nitrogen atmosphere. To the reaction mixture, 4-nitrophenol (45.5 mg, 0.3272 mmoles) was added and the reaction mixture was stirred for 2 hrs. The reaction mixture was quenched in ice cold water (50 mL) and extracted with ethyl acetate (2×25 ml). Ethyl acetate layer was washed with sodium bicarbonate solution (2×25 mL), 1N HCl (2×25 mL) and with brine, dried over sodium sulphate and concentrated to give 150 mg of the title compound.
Workup
- stirringthe reaction mixture was stirred for 2 hrs
- customThe reaction mixture was quenched in ice cold water (50 mL)
- extractionextracted with ethyl acetate (2×25 ml)
- washEthyl acetate layer was washed with sodium bicarbonate solution (2×25 mL), 1N HCl (2×25 mL) and with brine
- dry with materialdried over sodium sulphate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6bdbc1bea15b4112a1ed9661884e66cc
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07238725B2
Reaction notes
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