Diisopropylethylamine → 4-chloro-N-isobutoxypicolinamide

HRID 1922281Notes

Reaction equation

HRID 1922281 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9](Cl)=[O:10])[CH:4]=1.Cl.[CH2:13]([O:17][NH2:18])[CH:14]([CH3:16])[CH3:15].C(N(CC)C(C)C)(C)C>C1COCC1.O.CCOC(C)=O>[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([NH:18][O:17][CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[CH:4]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 12696238O-(2-Methylpropyl)hydroxylamine--hydrogen chloride (1/1)HCID 223972704-Chloropyridine-2-carbonyl chloride--hydrogen chloride (1/1)

Product 1

HCID 577256094-chloro-N-isobutoxypicolinamideYield 67%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-chloropicolinoyl chloride hydrochloride (1.0 g, 5.68 mmol, 1.0 eq) in 25 ml of THF were added O-isobutylhydroxylamin hydrochloride (785 mg, 6.25 mmol, 1.1 eq) and N,N-diisopropylethylamine (2.97 ml, 17.0 mmol, 3.0 eq) at room temperature. The reaction mixture was stirred for 30 min and diluted with water (25 mL) and EtOAc (50 mL). The separated organic layer was washed with brine (25 mL), saturated sodium bicarbonate solution (2×25 mL) and dried over sodium sulfate. Concentration under reduced pressure gave the title compound as colorless solid (870 mg, 67%), which was used without further purification. ES/MS m/z 229.0 (MH+), Rt=2.61 min.

Workup

  1. washThe separated organic layer was washed with brine (25 mL), saturated sodium bicarbonate solution (2×25 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-e2ff6f4919a74304b49dbe5409e22976
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Reaction notes

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