Methylamine → Methyl 6-(methylamino)-5-nitronicotinate

Reaction equation

Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[CH3:15][NH2:16]>>[CH3:15][NH:16][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1

Participants

Reactant 2

HCID 6329Methylamine

HCID 346961Methyl 6-chloro-5-nitronicotinate

Product 1

HCID 18412421Methyl 6-(methylamino)-5-nitronicotinate

Procedure

1.6 g (7.4 mmol) of methyl 6-chloro-5-nitronicotinate (see Bernie et al., J. Chem. Soc. 1951, 2590) were stirred in 20 mL of 40% aqueous methylamine solution at room temperature for 30 minutes. The reaction mixture was then diluted with ice water, the yellow precipitate formed was filtered off and dried. Yield: 1.2 g (80% of theory); Rf value: 0.66 (silica gel; ethyl acetate/ethanol/glacial acetic acid=90:5:5).

Workup

customthe yellow precipitate formed
filtrationwas filtered off
customdried

Sources & evidence

ORD record: ord-d965c41669614f89bb9338419eeebced
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06710055B2

Reaction notes

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