Water → 4-chloro-7-methoxy-N-methylquinoline-6-carboxamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([Cl:13])=[CH:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[C:14](Cl)=[O:15].COC1C=C2C(C(=O)C=[CH:25][NH:26]2)=CC=1C(O)=O.CN.O>O1CCCC1>[CH3:25][NH:26][C:14]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[O:2][CH3:1])[N:10]=[CH:9][CH:8]=[C:7]2[Cl:13])=[O:15]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
After dissolving 7-methoxy-4-chloro-quinoline-6-carbonyl chloride synthesized by the method of Production Example 152-2 from 7-methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylic acid (947 mg) in tetrahydrofuran (70 ml), the solution was cooled to 0° C. A 40% aqueous methylamine solution (0.4 ml) was added, and the mixture was stirred at room temperature for 30 minutes. Water was added, extraction was performed 3 times with ethyl acetate, and the organic layers were combined, washed with water and saturated brine, dried over sodium sulfate and then dried under reduced pressure to obtain the title compound (710 mg).
Workup
- extractionextraction
- washwashed with water and saturated brine
- dry with materialdried over sodium sulfate
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-1fe11766e2e84ae6a96cbfe24307d8f8
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07253286B2
Reaction notes
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