3-(Pyridin-4-yl)propanoic acid → 4-hydroxy-1-(3-nitrophenyl)-3-[1-oxo-3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one

HRID 1822192Notes

Reaction equation

HRID 1822192 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:4](=[O:21])[CH:3]=1.[N:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30](O)=[O:31])=[CH:24][CH:23]=1>>[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:4](=[O:21])[C:3]=1[C:30](=[O:31])[CH2:29][CH2:28][C:25]1[CH:26]=[CH:27][N:22]=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 2332433-(Pyridin-4-yl)propanoic acidHCID 546762034-hydroxy-1-(3-nitrophenyl)-1,8-naphthyridin-2(1H)-one

Product 1

HCID 673999274-hydroxy-1-(3-nitrophenyl)-3-[1-oxo-3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-oneYield 54%

Procedure

The procedure of Synthetic Example 1 was repeated using a mixture of 4-hydroxy-1-(3-nitrophenyl)-1,8-naphthyridin-2 (1H)-one (2.5 g, 8.83 mmol), 3-(pyridin-4-yl)propionic acid (19.87 g, 131 mmol, 15 eq.; prepared in Synthetic Example 1-(1)) and polyphosphoric acid (about 100 ml) to obtain 4-hydroxy-1-(3-nitrophenyl)-3-[1-oxo-3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2 (1H)-one (1.98 g, 54%).

Sources & evidence

ORD record
ord-f201856ddd73480e8552f46fd70c6dfb
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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