Tributylamine → 6-(6-cyano-2,2-dimethyl-2H-1-benzopyran-4-yl)-3-pyridinecarboxylic acid
Reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH:9]=[C:8]([C:14]3[N:19]=[CH:18][C:17]([C:20]([O:22]CC4C=CC=CC=4)=[O:21])=[CH:16][CH:15]=3)[C:7]=2[CH:30]=1)#[N:2].C(N(CCCC)CCCC)CCC>[Pd].C(O)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH:9]=[C:8]([C:14]3[N:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=3)[C:7]=2[CH:30]=1)#[N:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
5.06 g of benzyl 6-(6-cyano-2,2-dimethyl-2H-1-benzopyran-4-yl)-3-pyridinecarboxylate were heated at 100° C. with 7.8 ml of tributylamine, 244 mg of 10% palladium-on-charcoal and 0.9 ml of formic acid. After 12 hours a further 7.8 ml of tributylamine and 10 ml of formic acid were added. After 24 hours a further 2 ml of tributylamine and 3 ml formic acid were added. After 26 hours a further 170 mg of 10% palladium-on-charcoal, 2 ml tributylamine and 3 ml of formic acid were added. After 28 hours the mixture was evaporated and filtered. The filtrate was evaporated and the residue obtained was chromatographed on silica gel using ethyl acetate/petroleum ether (1:2) and ethyl acetate for the elution. There were obtained 1.4 g of 6-(6-cyano-2,2-dimethyl-2H-1-benzopyran-4-yl)-3-pyridinecarboxylic acid which was used without further purification.
Workup
- customAfter 28 hours the mixture was evaporated
- filtrationfiltered
- customThe filtrate was evaporated
- customthe residue obtained
- customwas chromatographed on silica gel
- washfor the elution
Sources & evidence
- ORD record
- ord-b552c8dbd6994d87ab472023c4036f89
- Source dataset
- uspto-grants-1992_06
- Patent number
- US05118694
Reaction notes
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