Sodium ethoxide → Sodium 3-(ethoxycarbonyl)-1,5-naphthyridine-2,4-bis(olate)

HRID 473417Notes

Reaction equation

HRID 473417 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]([NH:8][C:9]1[C:10]([C:15]([O:17]C)=O)=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:7])[CH3:2].C([O-])C.[Na+:23]>CCO>[CH2:1]([O:3][C:4]([C:5]1[C:6]([O-:7])=[N:8][C:9]2[C:10]([C:15]=1[O-:17])=[N:11][CH:12]=[CH:13][CH:14]=2)=[O:19])[CH3:2].[Na+:23].[Na+:23]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 67239641HCID 67239641, compound

Product 1

HCID 67240435Sodium 3-(ethoxycarbonyl)-1,5-naphthyridine-2,4-bis(olate)

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of methyl 3-(3-ethoxy-3-oxopropanamido)picolinate (3.7 g, 14.67 mmol) in EtOH (50 mL) was added sodium ethanolate (6.56 mL, 17.60 mmol). The reaction was stirred at rt for 1 h. After this time the reaction was concentrated in vacuo and dried under vacuum overnight to give sodium 3-(ethoxycarbonyl)-1,5-naphthyridine-2,4-bis(olate): 1H NMR (400 MHz, DMSO-d6) δ ppm 1H NMR (400 MHz, DMSO-d6) δ ppm 8.14 (1H, dd, J=4.5, 1.6 Hz), 7.46 (1H, dd, J=8.2, 1.6 Hz), 7.29 (1H, dd, J=8.2, 4.3 Hz), 4.08 (2H, q, J=7.0 Hz), 1.13-1.24 (3H, m).

Workup

  1. concentrationAfter this time the reaction was concentrated in vacuo
  2. customdried under vacuum overnight

Sources & evidence

ORD record
ord-3d5d678a86c946b6b2555b791939f7f1
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Reaction notes

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