TERT-BUTYL 2-CHLORONICOTINATE → HCID 22645509, compound

HRID 859239Notes

Reaction equation

HRID 859239 reaction equation
Cl[C:2]1[N:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[CH3:15][NH2:16].CO>>[CH3:15][NH:16][C:2]1[N:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

3

Reactant 2

HCID 11195236TERT-BUTYL 2-CHLORONICOTINATEHCID 57454252Monomethylamine methanol

Product 1

HCID 22645509HCID 22645509, compoundYield 92%

Procedure

t-Butyl 2-chloronicotinate (k) (50.0 g, 0.234 mol) was dissolved in a 40% methylamine-methanol solution (300 mL) and the mixture was stirred at room temperature for 30 h. The mixture was evaporated under reduced pressure and the resulting residue was dissolved in EtOAc (750 mL). The EtOAc solution was washed with water, dried over MgSO4 and evaporated under reduced pressure. The obtaining oily crude product was purified by a short silica gel column chromatography (ca. 300 g of silica gel, eluent: EtOAc/hexane=1/3) to give t-butyl 2-(N-methylamino)nicotinate (1) (45.0 g, ca. 92%) contaminated by starting meterial; 1H NMR (CDCl3): δ 1.57 (s, 9H), 3.05 (d, J=5.0 Hz, 3H), 6.49 (dd, J=4.6 and 7.6 Hz, 1H), 7.96 (bs, 1H), 8.04 (dd, J=2.0 and 7.6 Hz, 1H), 8.28 (dd, J=2.0 and 4.6 Hz, 1H).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in EtOAc (750 mL)
  3. washThe EtOAc solution was washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customThe obtaining oily crude product was purified by a short silica gel column chromatography (ca. 300 g of silica gel, eluent: EtOAc/hexane=1/3)

Sources & evidence

ORD record
ord-6ed74c4b7bc04db3921be1e290cbdbe8
Source dataset
uspto-grants-2006_12
Patent number
US07151182B2

Reaction notes

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