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

HRID 2288319Notes

Reaction equation

HRID 2288319 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

3

Reactant 2

HCID 6329MethylamineHCID 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-nitro-nicotinate (see Bernie et al. in 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

  1. customthe yellow precipitate formed
  2. filtrationwas filtered off
  3. customdried

Sources & evidence

ORD record
ord-0e9b5fc20a244dab93dc9b54e0b1be82
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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