Hydrochloric Acid → 6-Pyridin-3-yl-3-oxo-2,3,4,5-tetrahydropyridazine-4-carboxylic acid

HRID 2374779Notes

Reaction equation

C(OC1C=CC(C2CC(C(O)=O)C(=O)NN=2)=CC=1)C1C=CC=CC=1.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]2[CH:32]=[C:33]([C:38]([O:40]CC)=[O:39])[C:34](=[O:37])[NH:35][N:36]=2)[CH:26]=1.[OH-].[Na+].Cl>>[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]2[CH2:32][CH:33]([C:38]([OH:40])=[O:39])[C:34](=[O:37])[NH:35][N:36]=2)[CH:26]=1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 20527882Ethyl 3-oxo-6-(pyridin-3-yl)-2,3-dihydropyridazine-4-carboxylate

HCID 692188726-[4-(Benzyloxy)phenyl]-3-oxo-2,3,4,5-tetrahydropyridazine-4-carboxylic acid

Product 1

HCID 692186086-Pyridin-3-yl-3-oxo-2,3,4,5-tetrahydropyridazine-4-carboxylic acidYield 92.3%

Procedure

Working as in example 19 for the preparation of 6-[4-(benzyloxy)phenyl]-3-oxo-2,3,4,5-tetrahydropyridazine-4-carboxylic acid, but starting with 2 g of ethyl 6-pyridin-3-yl-3-oxo-2,3-dihydropyridazine-4-carboxylate, 24.5 cm3 of one molar sodium hydroxide solution and 25 cm3 of one molar hydrochloric acid solution, 1.65 g of 6-pyridin-3-yl-3-oxo-2,3,4,5-tetrahydropyridazine-4-carboxylic acid were obtained in the form of a cream-colored solid melting at a temperature above 260° C.

Sources & evidence

ORD record: ord-3087780167e14b13a8ec2aee743f6664
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07462613B2

Reaction notes

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