HCID 86600380, compound → GNF-Pf-4475
Reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][C:14]([O:16]CC)=O)=[CH:7][CH:6]=1)[CH3:2]>C1(C(C2C=CC=CC=2)=O)C=CC=CC=1.C(OCC)C>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[C:7]2[C:8](=[CH:9][CH:10]=1)[NH:11][C:12]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[CH:13][C:14]2=[O:16])=[O:25])[CH3:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 250 °C
Procedure
4-Amino-benzoic acid ethyl ester (66 g, 0.4 mol) and 3-oxo-3-phenyl-propionic acid ethyl ester (0.4 mol, 1 eq.) were dissolved in 500 mL cyclohexane and refluxed for 2 days using a Dean-Stark trap. The solution was filtered, the solvent evaporated and the residue recrystallized to give 4-(2-ethoxycarbonyl-1-phenyl-ethylideneamino)-benzoic acid ethyl ester (Compound 481a) MS: 340.18 (M+H+). 4-(2-Ethoxycarbonyl-1-phenyl-ethylideneamino)-benzoic acid ethyl ester was dissolved in diphenyl-methanone (250 mL) and heated to 250° C. for 4 hr. The resulting solution was diluted with diethyl ether and filtered to give 48.6 g of the title intermediate as a white crystalline solid.
Workup
- filtrationfiltered
Sources & evidence
- ORD record
- ord-a577073ebe364a4c82297261bf042f78
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07511145B2
Reaction notes
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