Sodium Nitrite → HCID 59547206, compound

HRID 1097189Notes

Reaction equation

HRID 1097189 reaction equation
[CH3:1][O:2][C:3]([C:5]1[Se:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[C:7]([N+:14]([O-])=O)[CH:6]=1)=[O:4].COC(C1[Se]C(C(OC)=O)=CC=1[NH2:26])=O.N([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+].[CH3:41][NH:42][CH3:43]>[Fe]>[CH3:41][N:42]([N:26]=[N:14][C:7]1[CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[Se:9][C:8]=1[C:10]([O:12][CH3:13])=[O:11])[CH3:43]

Participants

6

Reactant 4

HCID 23668193Sodium NitriteHCID 59547205HCID 59547205, compoundHCID 59547228HCID 59547228, compoundHCID 86646880HCID 86646880, compound

Product 1

HCID 59547206HCID 59547206, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Oxidation of methyl 5-methylselenophene-2-carboxylate with selenium dioxide provided methyl 5-formylselenophene-2-carboxylate, which on further oxidation with silver nitrate gave selenophene-2,5-dicarboxylic acid. Nitration of selenophene-2,5-dicarboxylic acid and esterfication provided methyl 5-(methoxycarbonyl)-3-nitroselenophene-2-carboxylate in good yield. The nitro functionality is reduced to amines using suitable reducing agents, for example, iron powder or any other nitro reducing agents in good yield. Diazotization of methyl-amino-5-(methoxycarbonyl)selenophene-2-carboxylate with sodium nitrite followed by treatment with potassium carbonate/dimethylamine provides methyl 3-[(dimethylamino)diazenyl]-5-(methoxycarbonyl)selenophene-2-carboxylate. Treatment of the ester with ammonia gave the required 3-[(dimethylamino)diazenyl]selenophene-2,5-dicarboxamide (compound 2).

Sources & evidence

ORD record
ord-8955b914fe9947fb86f6525b2edaf19c
Source dataset
uspto-grants-2012_03
Patent number
US08143237B2

Reaction notes

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