Hydrochloric Acid → 4-Sec-butyl-1,2-dihydro-6-methyl-2-oxopyridine-3-carbonitrile

HRID 85545ノート

反応式

HRID 85545 の反応式
CC([O-])(C)C.[K+].[C:7]([CH2:9][C:10]([NH2:12])=[O:11])#[N:8].[CH3:13][CH:14]([CH2:20][CH3:21])/[CH:15]=[CH:16]/[C:17](=O)[CH3:18].NCC1C(=O)NC(C)=CC=1CCC.O=O.Cl>CS(C)=O.O>[CH:14]([C:15]1[CH:16]=[C:17]([CH3:18])[NH:12][C:10](=[O:11])[C:9]=1[C:7]#[N:8])([CH2:20][CH3:21])[CH3:13]

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 977OxygenHCID 7898CyanoacetamideHCID 53645545-Methyl-3-hepten-2-oneHCID 23665647Potassium tert-butoxide2 回HCID 671241403-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-oneacetate

生成物 1

HCID 682102564-Sec-butyl-1,2-dihydro-6-methyl-2-oxopyridine-3-carbonitrile収率 53%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

To a stirred solution of t-BuOK (8 g, 71.42 mmol) and cyanoacetamide (6.6 g, 78.57 mmol) in DMSO (80 mL) was added (E)-5-methylhept-3-en-2-one, 2 (9 g, 71.42 mmol) under argon atmosphere at room temperature. The reaction mixture was stirred at room temperature for 1 h and then added additional t-BuOK (24 g, 214.28 mmol) was added. Then argon was displaced by oxygen and stirred at RT for 48 h. The reaction mixture was cooled to 0° C., diluted with water (36 mL) followed by 4N HCl (up to pH˜4) and the resulting reaction mixture was stirred for 15 min. The separated solid was collected by filtration, washed with water (10 mL), pet ether (100 mL) and dried to afford the title compound as yellow solid (7 g, 53%). 1H NMR (DMSO-d6, 400 MHz): δ 0.816-0.779 (t, 3H, J=7.6 Hz), 1.178-1.161 (d, 3H, J=6.8 Hz), 1637-1.505 (m, 2H), 2.24 (s, 3H), 2.814-2.760 (m, 1H), 6.239 (s, 1H), 12.324 (bs, 1H); LCMS (ES−) m/z=189.20 (M−H)

後処理

  1. additionwas added
  2. stirringstirred at RT for 48 h
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. customthe resulting reaction mixture
  5. stirringwas stirred for 15 min
  6. filtrationThe separated solid was collected by filtration
  7. washwashed with water (10 mL), pet ether (100 mL)
  8. customdried

出典と根拠

ORDレコード
ord-bdf06db785e841b8aa4c462587de416a
出典データセット
uspto-grants-2014_09
特許番号
US08846935B2

反応ノート

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