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Dimethylformamide → 5-Bromo-1-(cyclopropylmethyl)-1,2-dihydropyridin-2-one

HRID 470528
ノート
印刷プレビュー

反応式

HRID 470528 の反応式
[CH3:1][C:2]([O-])([CH3:4])[CH3:3].[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11](=[O:14])[NH:12][CH:13]=1.C1(CBr)CC1.CN(C)C=O>O1CCCC1.C(OCC)(=O)C>[Br:7][C:8]1[CH:9]=[CH:10][C:11](=[O:14])[N:12]([CH2:1][CH:2]2[CH2:4][CH2:3]2)[CH:13]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 81503BromomethylcyclopropaneHCID 5995285-Bromo-2-hydroxypyridineHCID 23665647Potassium tert-butoxide

生成物 1

HCID 596357015-Bromo-1-(cyclopropylmethyl)-1,2-dihydropyridin-2-one

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒
HCID 8857
Ethyl Acetate
溶媒

反応条件

温度
70 °C

実験手順

KOtBu (0.68 g) was added to a solution of 5-bromo-1H-pyridin-2-one (1.00 g) in tetrahydrofuran (20 mL) at room temperature. After stirring for 30 min, cyclopropylmethyl bromide (0.77 mL) and dimethylformamide (3 mL) were added to the suspension and the resulting mixture was warmed to 70° C. After stirring the mixture at 70° C. for 2 h, the reaction was complete. The mixture was cooled to room temperature, diluted with ethyl acetate (50 mL), and washed with water (2×20 mL) and brine (20 mL). Then, the solution was dried (MgSO4) and the solvent was removed to give the title compound as a colorless oil. Yield: 1.18 g (90% of theory). Mass spectrum (ESI+): m/z=228/230 (Br) [M+H]+

後処理

  1. stirringAfter stirring the mixture at 70° C. for 2 h
  2. temperatureThe mixture was cooled to room temperature
  3. washwashed with water (2×20 mL) and brine (20 mL)
  4. dry with materialThen, the solution was dried (MgSO4)
  5. customthe solvent was removed

出典と根拠

ORDレコード
ord-fac1a290a49b462493c37b3f0b0cbc27
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08629138B2

反応ノート

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