HCID 67313208, compound → HCID 67314085, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:12]=[N:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][C:15]=3[N+:21]([O-])=O)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1>C(O)(=O)C.[Fe]>[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:12]=[N:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][C:15]=3[NH2:21])(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 110 °C
Procedure
10.13 g of 3-(3-fluorophenylsulfonyl)-8-nitroquinoline (30.5 mmol) were suspended in 150 ml of acetic acid and warmed to 110° C. 8.51 g of iron powder (152 mmol) were added in small portions with stirring. Stirring was continued for 1 h. Then, the reaction mixture was cooled to room temperature, partitioned between water and ethyl acetate. The organic phase was separated and the aqueous layer was extracted three times with ethyl acetate. Water was added to the combined organic layers and the pH was adjusted to alkaline conditions with aqueous ammonia solution under rapid stirring. The organic layer was separated, extracted twice with water, dried over magnesium sulfate, filtered and the solvents were evaporated to yield 9.2 g of the product.
Workup
- stirringStirring
- temperatureThen, the reaction mixture was cooled to room temperature
- custompartitioned between water and ethyl acetate
- customThe organic phase was separated
- extractionthe aqueous layer was extracted three times with ethyl acetate
- additionWater was added to the combined organic layers
- customThe organic layer was separated
- extractionextracted twice with water
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customthe solvents were evaporated
Sources & evidence
- ORD record
- ord-f6810640f58e4a15aa71e9a458acc58d
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08440694B2
Reaction notes
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