Methyl 2-anilinopyridine-3-carboxylate → 3-Butyl-4-hydroxy-1-[3-(methylsulfanyl)phenyl]-1,8-naphthyridin-2(1H)-one

HRID 1248944Notes

Reaction equation

[CH2:1]([C:5]1[C:6](=[O:22])[N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:2][CH2:3][CH3:4].[CH3:23][S:24]C1C=C(NC2C(C(OC)=O)=CC=CN=2)C=CC=1.C1(NC2C(C(OC)=O)=CC=CN=2)C=CC=CC=1>>[CH2:1]([C:5]1[C:6](=[O:22])[N:7]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]([S:24][CH3:23])[CH:21]=2)[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:2][CH2:3][CH3:4]

Participants

Reactant 3

HCID 10998755Methyl 2-anilinopyridine-3-carboxylate

HCID 13506724Methyl 2-[3-(methylsulfanyl)anilino]pyridine-3-carboxylate

HCID 54704755Sch 12223

Product 1

HCID 547102493-Butyl-4-hydroxy-1-[3-(methylsulfanyl)phenyl]-1,8-naphthyridin-2(1H)-one

Procedure

Prepare the 3-(n-butyl)-4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)one by the process of Example 1 by replacing the methyl 2-(3-methylthiophenylamino)-3-pyridine carboxylate with an equivalent amount of methyl 2-phenylamino-3-pyridine carboxylate.

Sources & evidence

ORD record: ord-564ed98fa66c4d2b99464f578864fd03
Source dataset: uspto-grants-1986_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04628055

Reaction notes

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