Methylamine → N,6-Dimethyl-5-nitropyridin-2-amine

Reaction equation

Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.[CH3:12][NH2:13]>>[CH3:12][NH:13][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[N:7]=1

Participants

Reactant 2

HCID 6329Methylamine

HCID 2531236-Chloro-2-methyl-3-nitropyridine

Product 1

HCID 13567018N,6-Dimethyl-5-nitropyridin-2-amine

Procedure

6-Chloro-2-methyl-3-nitro-pyridine (0.6 g) was treated with methyl amine according to General Procedure U to give methyl-(6-methyl-5-nitro-pyridin-2-yl)-amine LCMS (m/z): 168. This was reduced under hydrogen atmosphere according to General Procedure Z to give 6,N*2*-dimethyl-pyridine-2,5-diamine (0.35 g), LCMS (m/z): 138. This was converted to 2-methyl-6-methylamino-pyridine-3-sulfonyl chloride according to General Procedure AA.

Sources & evidence

ORD record: ord-b4a6123f598e41ce9e1d3fa0f678710e
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987295B2

Reaction notes

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