Sodium Nitrite → HCID 59547219, compound

HRID 1097188Notes

Reaction equation

HRID 1097188 reaction equation
[CH3:1][C:2]1[Se:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][C:3]=1[N+:11]([O-])=O.CC1C([NH2:24])=C(C([O-])=O)[Se]C=1C.N([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+].[CH3:35][NH:36][CH3:37]>[Fe]>[CH3:35][N:36]([N:24]=[N:11][C:3]1[CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[Se:6][C:2]=1[CH3:1])[CH3:37]

Participants

6

Reactant 4

HCID 23668193Sodium NitriteHCID 59547210HCID 59547210, compoundHCID 86646878HCID 86646878, compoundHCID 86646880HCID 86646880, compound

Product 1

HCID 59547219HCID 59547219, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Nitration of methyl 5-methylselenophene-2-carboxylate provided methyl 5-methyl-4-nitroselenophene-2-carboxylate. 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-methylselenophene-2-carboxylate with sodium nitrite followed by treatment with potassium carbonate/dimethylamine provides methyl 4-[(dimethylamino)diazenyl]-5-methylselenophene-2-carboxylate. Treatment of the ester with ammonia gave the required 4-[(dimethylamino)diazenyl]-5-methylselenophene-2-carboxamide (compound 1).

Sources & evidence

ORD record
ord-aafc9be4372f4c36aa81ef1b75cc52b5
Source dataset
uspto-grants-2012_03
Patent number
US08143237B2

Reaction notes

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