3-(Dimethylaminomethylidene)-6-methylpyran-2,4-dione → 4-Hydroxy-6-methyl-nicotinic acid

HRID 359588Notes

Reaction equation

C[N:2]([CH:4]=[C:5]1[C:10](=[O:11])[CH:9]=[C:8]([CH3:12])[O:7][C:6]1=[O:13])C>[OH-].[NH4+]>[CH3:12][C:8]1[NH:2][CH:4]=[C:5]([C:6]([OH:7])=[O:13])[C:10](=[O:11])[CH:9]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3-(dimethylaminomethylene)-4-oxo-6-methyl-2-pyrone (85.0 g) and ammonium hydroxide (500 ml) is slowly heated to 70° C. with the condenser outlet open. The mixture is heated at 70°-80° C. for 3 hours, concentrated to a volume of about 100 ml and acidified with 3N HCl to pH 5. The product is filtered and washed with water and diethyl ether to give 38.6 g of the title compound. Physical characteristics are as follows:

Workup

temperatureThe mixture is heated at 70°-80° C. for 3 hours
concentrationconcentrated to a volume of about 100 ml
filtrationThe product is filtered
washwashed with water and diethyl ether

Sources & evidence

ORD record: ord-f7a7750359364b7e901b9f07649a0bbc
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05001235

Reaction notes

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