4-Methoxy-8-nitro-dibenzo[b,d]furan-1-carboxylic acid → 4-Methoxy-8-chloro-dibenzo[b,d]furan-1-carboxylic acid
Reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][C:13]([N+]([O-])=O)=[CH:12][C:11]=3[C:7]=2[C:6]([C:19]([OH:21])=[O:20])=[CH:5][CH:4]=1.[ClH:22].O.N([O-])=O.[Na+]>O.Cl.Cl[Cu]>[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][C:13]([Cl:22])=[CH:12][C:11]=3[C:7]=2[C:6]([C:19]([OH:21])=[O:20])=[CH:5][CH:4]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
Intermediate 29 (350 mg, 1.13 mmol) was suspended in mixture of concentrated hydrochloric acid:water (1: 1) (5 ml) and stirred at 50° C. for 30 min. The suspension was cooled to 0° C. and a solution of sodium nitrite (83 mg, 1.2 mmol) in water (2 ml) was added dropwise in 15 min. The reaction was stirred for 90 min. at 0-5° C. and then this suspension was added to a pre-cooled solution of CuCl (123 mg, 1.24 mmol) in concentrated HCl (5 ml). The reaction was allowed to come to room temperature and further heated to 80-90° C. for 2 h. The reaction mixture was then poured into water (100 ml) and the solid was filtered and then purified by column chromatography using 20% ethyl acetate-chloroform as the eluent to obtain 250 mg of the product as white solid; mp: 264-276° C.
Workup
- temperatureThe suspension was cooled to 0° C.
- stirringThe reaction was stirred for 90 min. at 0-5° C.
- customto come to room temperature
- temperaturefurther heated to 80-90° C. for 2 h
- filtrationthe solid was filtered
- custompurified by column chromatography
Sources & evidence
- ORD record
- ord-6d9bc60a176c499b87ac73b0efc397b6
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07238725B2
Reaction notes
Loading…