Hydrochloric Acid → 1-Benzyl-4-(benzyloxy)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylic acid

HRID 1179326Notes

Reaction equation

[CH2:1]([N:8]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:10]([C:26]([O:28]C)=[O:27])[C:9]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O.Cl>C1COCC1>[CH2:1]([N:8]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:10]([C:26]([OH:28])=[O:27])[C:9]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 1-benzyl-4-(benzyloxy)-2-oxo-1,2-dihydro-1,5naphthyridine-3-carboxylate (0.65 g, 1.62 mmol) in THF (20 mL) was added sodium hydroxide (16.2 mL, 1 N) and the solution was heated to 80° C. and after 1.5 hours the reaction was completed. The reaction was allowed to cool and then the THF was removed leaving the product in water. The water was acidified with 1N HCl to adjust the pH to 3 and the resulting crude solids were collected by vacuum filtration and taken on as is.

Workup

temperatureto cool
customthe THF was removed
customleaving the product in water
filtrationthe resulting crude solids were collected by vacuum filtration

Sources & evidence

ORD record: ord-1f1e445520c040b2a9fad9cf0e0ee5e8
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279487B2

Reaction notes

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