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Acetic Acid → 5-(6-Oxo-5,6,7,8-tetrahydro-[1,5]naphthyridin-2-yl)-nicotinic acid methyl ester

HRID 1774796
Notes
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Reaction equation

HRID 1774796 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[C:13]([CH:20]=[CH:21][C:22]([O:24]C)=O)[N:12]=2)[CH:8]=[N:9][CH:10]=1)=[O:4].CC(O)=O>CO.[Pd]>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]3[NH:17][C:22](=[O:24])[CH2:21][CH2:20][C:13]=3[N:12]=2)[CH:8]=[N:9][CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 866791606-(2-Methoxycarbonyl-vinyl)-5-nitro-[2,3']bipyridinyl-5'-carboxylic acid methyl ester

Product 1

HCID 866791595-(6-Oxo-5,6,7,8-tetrahydro-[1,5]naphthyridin-2-yl)-nicotinic acid methyl esterYield 65.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887Methanol
Solvent

Conditions

Temperature
50 °C

Procedure

6-(2-Methoxycarbonyl-vinyl)-5-nitro-[2,3′]bipyridinyl-5′-carboxylic acid methyl ester (926 mg, 2.7 mmol), 10% Pd/C (300 mg) and AcOH (1.3 mL) were suspended in methanol (300 mL) and the reaction mixture was stirred at 50° C. under 50 psi H2 pressure for 13 hours. After filtration, the reaction mixture was concentrated in vacuo to give a crude product of 5-(6-oxo-5,6,7,8-tetrahydro-[1,5]naphthyridin-2-yl)-nicotinic acid methyl ester (500 mg, 65.4%) as a light yellow solid. MS: 284.1 (M+H+).

Workup

  1. filtrationAfter filtration
  2. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-c1bbe9bbe06f467c83d5ea7871c0b6af
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09260408B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes