Ethyl Acetoacetate → HCID 12713139, compound
Reaction equation
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16](OCC)(=[O:21])[CH2:17][C:18]([CH3:20])=O.[F:25][C:26]([F:36])([F:35])[C:27](=O)[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>[Cl-].[Zn+2].[Cl-].C(O)C>[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]2[C:12]([C:18]([CH3:20])=[CH:17][C:16](=[O:21])[O:15]2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:1]([NH:8][C:9]1[CH:10]=[C:32]2[C:33]([C:27]([C:26]([F:36])([F:35])[F:25])=[CH:28][C:29](=[O:30])[O:31]2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 3
Product 2
Reagents, catalysts & solvents 2
Procedure
According to this invention, water-soluble coumarins and azacoumarins having the structures: ##STR2## wherein R is CH3 or CF3 and wherein R1 is H or CH3 are prepared. The coumarins are prepared by means of a three step process involving (1) heating resorcinol and benzylamine to form 3-benzylaminophenol, (2) reacting the 3-benzylaminophenol with ethyl acetoacetate or ethyl trifluoroacetoacetate in the presence of anhydrous zinc chloride and absolute ethanol to form 7-benzylamino-4-methylcoumarin or 7-benzylamino-4-trifluoromethylcoumarin, (3) sulfonating the product of step (2) with oleum and (4) neutralizing the sulfonate formed in step (3) with sodium bicarbonate. The azacoumarins are prepared by a similar process except that 6-chloro-2-pyridinol and either benzylamine or benzylmethylamine are used as the starting compounds (the step (1) reactants).
Sources & evidence
- ORD record
- ord-e132bb2a8aa249bfa1df2e774c63ccd8
- Source dataset
- uspto-grants-1980_04
- Patent number
- US04200753
Reaction notes
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