Biphenyl → N-(3-Cyano-6-methoxy-4-oxo-1,4-dihydro-7-quinolinyl)acetamide
Reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[NH:8]/[CH:9]=[C:10](\[C:16]#[N:17])/[C:11]([O:13]CC)=O)(=[O:3])[CH3:2].C(NC1C=C(C=CC=1OC)N/C=C(/C#N)\C(OCC)=O)(=O)C.C1(C2C=CC=CC=2)C=CC=CC=1.C1(OC2C=CC=CC=2)C=CC=CC=1>C(OCC)C>[C:16]([C:10]1[C:11](=[O:13])[C:18]2[C:7](=[CH:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[C:20]([O:21][CH3:22])[CH:19]=2)[NH:8][CH:9]=1)#[N:17]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 256 °C
Procedure
An amount of 1 g (0.003 mol) of a mixture of ethyl (E)-3-[3-(acetylamino)-4-methoxyanilino]-2-cyano-2-propenoate and ethyl (Z)-3-[3-(acetylamino)-4-methoxyanilino]-2-cyano-2-propenoate was added to a stirring solution of biphenyl (16.3 mL, 0.10 mol) and phenyl ether (48.8 mL, 0.30 mol) at 256° C. After stirring for 2 hours at 256° C., the reaction mixture was cooled to room temperature, diluted with diethyl ether (130 mL), filtered, and evaporated to dryness to give a gray solid (0.53 g, 62% yield), mp 305-310° C.; 1H NMR (DMSO-d6) δ 12.80 (s, 1H), 9.58 (s, 1H), 8.62 (s, 1H), 8.58 (m, 1H), 7.52 (s, 1H), 3.97 (s, 3H), 2.20 (s, 3H); HRMS (EI) m/z 257.0793 (M+1).
Workup
- temperaturethe reaction mixture was cooled to room temperature
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-49d29ee9b1fe49a89d3c336dd99a9581
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06608048B2
Reaction notes
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