Hydrochloric Acid → HCID 54720033, compound

HRID 2364138Notes

Reaction equation

HRID 2364138 reaction equation
[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:23])=[C:13]([C:19](OC)=[O:20])[C:14](=[O:18])[NH:15]2)=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:25][OH:26].C[O-].[Na+].CO.Cl>O.CCO.O>[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:23])=[C:13]([C:19]([NH:25][OH:26])=[O:20])[C:14](=[O:18])[NH:15]2)=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 23694274Sodium methanolate methanolHCID 54729995HCID 54729995, compound

Product 1

HCID 54720033HCID 54720033, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

A mixture of methyl 7-benzyl-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (21 mg, 68 μmol), hydroxylamine hydrochloride (75 mg, 1.1 mmol) and 4.63 M NaOMe/MeOH (0.1 mL, 463 μmol) in 4:1 EtOH/water (1.25 mL) was heated at reflux for 2 h. The mixture was neutralized with conc. HCl, diluted with water and the resulting solids were collected by filtration. Trituration of the filter cake with EtOAc/MeOH provided the product as a beige solid: 1H NMR (d6-DMSO) δ 11.86 (2H, br), 9.78 (1H, br), 8.50 (1H, br), 7.50-7.10 (6H, m), 4.10 (2H, br s); HRMS calcd for C16H13N3O4+H+: 312.0984. Found: 312.0987.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. filtrationthe resulting solids were collected by filtration

Sources & evidence

ORD record
ord-6236ae7571f6495998b05e6086ffd4ee
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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