Chloroacetic Acid → (5-Oxo-1,6-naphthyridin-6(5H)-YL)acetic acid

HRID 887109Notes

Reaction equation

[N:1]1[C:10]2[CH:9]=[CH:8][NH:7][C:6](=[O:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl[CH2:15][C:16]([OH:18])=[O:17].Cl>>[O:11]=[C:6]1[N:7]([CH2:15][C:16]([OH:18])=[O:17])[CH:8]=[CH:9][C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]1=2

Participants

Reactant 4

HCID 300Chloroacetic Acid

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 55203681,6-naphthyridin-5(6H)-one

Product 1

HCID 57907423(5-Oxo-1,6-naphthyridin-6(5H)-YL)acetic acid

Conditions

Temperature: 100 °C

Procedure

To 1,6-naphthyridin-5(6H)-one (0.625 g, 4.28 mmol) was added 5 M sodium hydroxide solution (1.7 mL) followed by chloroacetic acid (0.404 g, 4.28 mmol). The reaction mixture was heated at 100° C. for 2 h. After cooled down to ambient temperature and neutralized with 2 N hydrochloric acid (2.1 mL), the title compound was collected by filtration as a yellow solid. 1H NMR (DMSO-d6): δ 13.1 (s, 1H), 8.94 (dd, J=4.6, 1.8 Hz, 1H), 8.51 (dd, J=8.0, 1.6 Hz, 1H), 7.72 (d, J=7.6 Hz, 1H), 7.52 (dd, J=8.0, 4.6 Hz, 1H), 6.72 (d, J=7.6 Hz, 1H), 4.72 (s, 2H). LC/MS 205.2 (M+1).

Workup

filtrationthe title compound was collected by filtration as a yellow solid

Sources & evidence

ORD record: ord-a0492798366f47e0935556308f54fdd0
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247415B2

Reaction notes

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