Perchloric Acid → Tert-butyl 2,6-dichloro-4-methylnicotinate

HRID 1481959Notes

Reaction equation

HRID 1481959 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=[O:5].Cl(O)(=O)(=O)=O>C(OC(C)(C)C)(=O)C.C(Cl)Cl>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4]([O:6][C:3]([CH3:7])([CH3:4])[CH3:2])=[O:5]

Participants

5

Reactant 2

HCID 24247Perchloric AcidHCID 6761212,6-Dichloro-4-methylpyridine-3-carboxylic acid

Product 1

HCID 117632239Tert-butyl 2,6-dichloro-4-methylnicotinateYield 190.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10908tert-Butyl acetateSolvent

Procedure

To a solution of 2,6-dichloro-4-methylnicotinic acid (1.00 g, 4.85 mmol, 1 equiv) in tert-butyl acetate (24 mL) was added 70% perchloric acid (0.88 mL, 14.56 mmol, 3 equiv). After 1 h, reaction was diluted with DCM, washed cautiously with saturated aqueous sodium bicarbonate solution, dried (Na2SO4), and concentrated in vacuo to provide the product (1.21 g, 95%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.15 (s, 1H), 2.37 (d, J=0.5 Hz, 3H), 1.62 (s, 9H); LCMS (ESI, M+1): 262.1.

Workup

  1. customreaction
  2. washwashed cautiously with saturated aqueous sodium bicarbonate solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4123f99c62c3415e82f82478e9dc7789
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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