N-Methylisopropylamine → HCID 43166595, compound

HRID 2047281Notes

Reaction equation

HRID 2047281 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[N:10]=1)[C:5]([OH:7])=[O:6].[CH:12]([NH:15][CH3:16])([CH3:14])[CH3:13]>O>[Cl:11][C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([N:15]([CH:12]([CH3:14])[CH3:13])[CH3:16])[N:10]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 78485N-MethylisopropylamineHCID 948302,6-Dichloroisonicotinic acid

Product 1

HCID 43166595HCID 43166595, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,6-dichloro-isonicotinic acid (572 mg, 2.98 mmol) in isopropyl-methylamine (2.18 g, 29.8 mmol) is stirred at 80° C. for 10 days. The mixture is cooled to rt, diluted with water (50 mL), and extracted with diethyl ether (6×50 mL). The aq. phase is acidified and extracted with diethyl ether (3×50 mL). The org. extracts are combined, dried over MgSO4, filtered and concentrated. The crude product is purified by MPLC on silica gel eluting with a gradient of EA in heptane to give the title compound (461 mg) as a yellow powder; LC-MS: tR=0.92 min, [M+1]+=229.01; 1H NMR (CD3OD): δ 1.19 (d, J=6.7 Hz, 6H), 2.88 (s, 3H), 4.78-4.87 (m, 1H), 6.94 (s, 1H), 7.01 (s, 1H).

Workup

  1. temperatureThe mixture is cooled to rt
  2. extractionextracted with diethyl ether (6×50 mL)
  3. extractionextracted with diethyl ether (3×50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by MPLC on silica gel eluting with a gradient of EA in heptane

Sources & evidence

ORD record
ord-63fb28bdf49549b6829d7b2759ef2eff
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

Loading…