5-Nitrofuroyl chloride → Sulfuric Acid
Reaction equation
[OH2:1].C[O:3][C:4]1C=[CH:8][C:7](N([S:12]([O-:15])(=[O:14])=[O:13])N)=[CH:6][CH:5]=1.[Na+].[N+](C1OC(C(Cl)=O)=CC=1)([O-])=[O:18]>O.C(O)(C)(C)C>[C:4]([OH:3])(=[O:18])[CH2:5][CH2:6][C:7]([CH3:8])=[O:1].[S:12](=[O:13])(=[O:18])([OH:14])[OH:15]Participants
Reactant 2
Product 2
Reagents, catalysts & solvents 2
Procedure
25.8 G. (0.1-mole) of sodium p-methoxyphenyl-hydrazine-sulphonate monohydrate are dissolved in a mixture of 112 ml of water and 48 ml of tert. butanol, then 17.4 g. (0.1 mole) of 5-nitro-furan-2-carboxylic acid chloride are poured into the solution, and the mixture is stirred for an hour at room temperature and consecutively for another hour on a water-bath of 70°-80°C. Subsequently, without isolating the product, 17 ml of levulinic acid and 4.5 ml of concentrated sulphuric acid are added dropwise, the mixture is stirred at 80°-85°C for an hour, cooled and 80 ml of water are added. The precipitated 1-(5-nitro-2-furoyl)-2-methyl-5-methoxy-indole-3-yl acetic acid is filtered by suction, and washed consecutively with 80 ml of 60% acetic acid and 100 ml of water. The crude product is recrystallized from 170 ml of 88% tert. butanol, clarified with 5% of active carbon "Norit", recrystallized on cooling, filtered by suction, washed with 20 ml of 88% tert. butanol, and dried to afford 17.7 g. of 1-(5-nitro-2-furoyl)-2-methyl-5-methoxy-indole-3-yl acetic acid. Yield 73.5%, m.p. 178°-180°C.
Sources & evidence
- ORD record
- ord-97498f2c55354237b1032ea46eb92d87
- Source dataset
- uspto-grants-1976_06
- Patent number
- US03964894
Reaction notes
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