methyl-(E)-4-(2'-fluoro-5'-chlorophenyl)-4-oxo-butenoate → Methyl 4-(2'-fluoro-5'-chlorobenzoyl)-5-hydroxynicotinate

HRID 234803Notes

Reaction equation

HRID 234803 reaction equation
[CH3:1][O:2][C:3](=[O:16])/[CH:4]=[CH:5]/[C:6]([C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[F:15])=[O:7].C([O:19][C:20]1O[C:23](C(O)=O)=[N:22][CH:21]=1)C>>[OH:19][C:20]1[CH:21]=[N:22][CH:23]=[C:4]([C:5]=1[C:6](=[O:7])[C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[F:15])[C:3]([O:2][CH3:1])=[O:16]

Participants

3

Reactant 2

HCID 10562170methyl-(E)-4-(2'-fluoro-5'-chlorophenyl)-4-oxo-butenoateHCID 124355045-Ethoxyoxazole-2-carboxylic acid

Product 1

HCID 10710045Methyl 4-(2'-fluoro-5'-chlorobenzoyl)-5-hydroxynicotinate

Procedure

Diels-Alder reaction of intermediate (XX) with the known 5-ethoxyoxazole-2-carboxylic acid (XXI) (step w) to give methyl 5-hydroxy-4-(2'-fluoro-5'-chlorobenzoyl)nicotinate (XXII);

Sources & evidence

ORD record
ord-5ccf716adbd0451eab6f08d1bbf3e88c
Source dataset
uspto-grants-1997_01
Patent number
US05596097

Reaction notes

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