Ammonia → HCID 178433459, compound

HRID 974080Notes

Reaction equation

[CH3:1][CH:2](C(C)=O)[C:3](OCC)=[O:4].N.[NH2:12]/[C:13](/[CH3:21])=[C:14](/[CH3:20])\[C:15]([O:17]CC)=O.CC(C(OCC)=O)C(OCC)=O>>[CH3:21][C:13]1[C:14]([CH3:20])=[C:15]([OH:17])[C:2]([CH3:1])=[C:3]([OH:4])[N:12]=1

Participants

Reactant 4

HCID 222Ammonia

HCID 701Ethyl 2-methylacetoacetate

HCID 11857Diethyl methylmalonate

HCID 53642952(Z)-3-Amino-2-methyl-2-butenoic Acid Ethyl Ester

Product 1

HCID 178433459HCID 178433459, compound

Procedure

U.S. Pat. No. 4,785,113 discloses the preparation of the title compounds from ethyl 2-methylacetoacetate by reaction with NH3 to give ethyl 3-amino-2-methylcrotonate, reaction with diethyl monomethylmalonate to give 2,3,5-trimethyl-4,6-dihydroxypyridine, chlorination to give 2,4-dichloro-3,5,6-trimethylpyridine, selective cleavage of the 2-Cl substituent and exchange of the 4-Cl substituent for a methoxy group, and then oxidation to give the N-oxide. The subsequent reactions are carried out analogously to the process described in U.S. Pat. No. 4,472,409.

Workup

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Sources & evidence

ORD record: ord-cb7d05be45c3484b8aaa327e8ac1c7b8
Source dataset: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05066810

Reaction notes

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