Methylamine → HCID 10512252, compound

HRID 878391Notes

Reaction equation

HRID 878391 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[N:6][C:5]=1Cl.CN.[CH:15]([N:18](C(C)C)CC)(C)C>>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[N:6][C:5]=1[NH:18][CH3:15]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 11106516Methyl 2,6-dichloropyridine-3-carboxylate

Product 1

HCID 10512252HCID 10512252, compound

Procedure

A solution of 2,6-dichloro-nicotinic acid methyl ester (1.5 g), methylamine (0.99 ml) (33% by weight in ethanol) and diisopropylethylamine (“Hunig's base”) (1.38 ml) was heated in a microwave for 10 minutes at 120° C. The reaction mixture was partitioned between ethyl acetate and water. The phases were separated and the organic layer was concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane 1:9) to give 6-chloro-2-methylamino-nicotinic acid methyl ester as a white solid (915 mg). 1H-NMR (400 MHz, CDCl3): 8.03 (bs, 1H), 7.99-8.01 (d, 1H), 6.49-6.51 (d, 1H), 3.86 (s, 3H), 3.05-3.06 (d, 3H) ppm.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe phases were separated
  3. concentrationthe organic layer was concentrated
  4. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane 1:9)

Sources & evidence

ORD record
ord-028295a511b64581841e1e65673f3be2
Source dataset
uspto-grants-2015_03
Patent number
US08987455B2

Reaction notes

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