Diisopropylethylamine → 4-chloro-N-isobutoxypicolinamide

HRID 1922281ノート

反応式

HRID 1922281 の反応式
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

参加物

7

反応物 3

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

生成物 1

HCID 577256094-chloro-N-isobutoxypicolinamide収率 67%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e2ff6f4919a74304b49dbe5409e22976
出典データセット
uspto-grants-2012_05
特許番号
US08173689B2

反応ノート

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