6-Chloro-2-methyl-3-nitropyridine → 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.[CH:12]1([NH:15]C)CC1>>[CH3:12][NH:15][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 2531236-Chloro-2-methyl-3-nitropyridine

HCID 11029756N-Methylcyclopropanamine

Product 1

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

Procedure

6-Chloro-2-methyl-3-nitro-pyridine (0.5 g) was treated with cyclopropyl-methylamine according to General Procedure U to give methyl-(6-methyl-5-nitro-pyridin-2-yl)-amine. LCMS (m/z): 208. This was reduced under hydrogen atmosphere according to General Procedure Z to give N*2*-cyclopropylmethyl-6-methyl-pyridine-2,5-diamine (0.35 g), LCMS (m/z): 178. This was converted to 6-(cyclopropylmethyl-amino)-2-methyl-pyridine-3-sulfonyl chloride according to General Procedure AA. LCMS (m/z): 261.

Sources & evidence

ORD record: ord-71ffc137bc3c49968d5870b0303ff9aa
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383644B2

Reaction notes

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