Nitric Acid → 3,4-Diethoxycarbonyl-6-methyl-5-nitro-2-pyridone

HRID 37475Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:18])[NH:8][C:9]([CH3:17])=[CH:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:5])[CH3:2].[N+:19]([O-])([OH:21])=[O:20].O>C(OC(=O)C)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:18])[NH:8][C:9]([CH3:17])=[C:10]([N+:19]([O-:21])=[O:20])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:5])[CH3:2]

Participants

Conditions

Temperature: -10 °C

Procedure

In 13 ml of acetic anhydride was suspended 5.0 g of 3,4-diethyoxycarbonyl-6-methyl-2-pyridone, and the suspension was cooled to -10° C., whereto 1.22 ml (2.1 eq.) of fuming nitric acid was added dropwise over 30 minutes. The mixture was stirred for 30 minutes. After 40 ml of water was added, the mixture was stirred overnight at room temperature. The resulting crystals were collected by filtration and dried.

Workup

stirringthe mixture was stirred overnight at room temperature
filtrationThe resulting crystals were collected by filtration
customdried

Sources & evidence

ORD record: ord-d3996878e0a04f65bd236c12d7592a0c
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420275

Reaction notes

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