Hydrochloric Acid → Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

HRID 2364130Notes

Reaction equation

HRID 2364130 reaction equation
CC[O-].[Na+].[CH2:5]([O:7][C:8](=[O:32])[CH2:9][C:10]([NH:12][C:13]1[C:14]([C:27]([O:29]CC)=O)=[N:15][CH:16]=[C:17]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH:18]=1)=[O:11])[CH3:6].Cl>CCO>[F:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C:17]2[CH:18]=[C:13]3[C:14]([C:27]([OH:29])=[C:9]([C:8]([O:7][CH2:5][CH3:6])=[O:32])[C:10](=[O:11])[NH:12]3)=[N:15][CH:16]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 42637836Ethyl 3-[(3-ethoxy-3-oxopropanoyl)amino]-5-(4-fluorobenzyl)pyridine-2-carboxylate

Product 1

HCID 54729997Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A 2M solution of NaOEt in EtOH (5.87 mL, 11.74 mmol) was added to a solution of ethyl 3-[(3-ethoxy-3-oxopropanoyl)amino]-5-(4-fluorobenzyl)pyridine-2-carboxylate (2.28 g, 5.87 mmol) in EtOH (23 mL) and the mixture was stirred at rt for 1 h. The mixture was neutralized with conc. HCl and concentrated in vacuo. Trituration of the resulting material with a mixture of EtOH and 1:1 brine/water followed by filtration afforded the product as a beige solid: 1H NMR (d6-DMSO) δ 11.54 (1H, br s), 8.54 (1H, d, J=1.4 Hz), 7.44 (1H, s), 7.32 (2H, dd, J=8, 6 Hz), 7.17 (2H, t, J˜9 Hz), 4.23 (2H, q, J=7 Hz), 4.12 (2H, s), 1.26 (3H, t, J=7 Hz); HRMS calcd for C18H15FN2O4+H+: 343.1094. Found: 343.1088.

Workup

  1. concentrationconcentrated in vacuo
  2. additionTrituration of the resulting material with a mixture of EtOH and 1:1 brine/water
  3. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-ab4113ea738a4dfb96295b924eb07cec
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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