Hydrochloric Acid → 8-hydroxy-1,6-Naphthyridine-7-carboxylic acid

HRID 1760162Notes

Reaction equation

[OH:1][C:2]1[C:3]([C:12]([O:14]C)=[O:13])=[N:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[OH-].[Li+].Cl>CO>[OH:1][C:2]1[C:3]([C:12]([OH:14])=[O:13])=[N:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

Conditions

Temperature: 100 °C

Procedure

To a slurry of methyl 8-hydroxy-1,6-naphthyridine-7-carboxylate from Example 1, Step 2 (1.50 g, 7.35 mmol) in methanol (45 ml) was added lithium hydroxide (22.0 ml of a 1M aq. solution, 22.0 mmol) and the reaction was heated at 100° C. for 7 hrs. Upon cooling to room temperature, hydrochloric acid (22.0 ml of a 1M aq. solution, 22.0 mmol) was added and the reaction stirred for 16 hrs. The mixture was concentrated to a volume of 50 ml and neutralized with dilute NaHCO3 (pH=7). The resulting precipitate was collected by filtration and washed with water and dried in vacuo to afford the title compound.

Workup

temperatureUpon cooling to room temperature
concentrationThe mixture was concentrated to a volume of 50 ml and neutralized with dilute NaHCO3 (pH=7)
filtrationThe resulting precipitate was collected by filtration
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-d1e11fd50d3347c2a972d07a39605578
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06841558B2

Reaction notes

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