Potassium Carbonate → 2,6-Dimethyl-5-nitroquinoline

HRID 2088469

反応式

HRID 2088469 の反応式
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:15])[C:8]=2[N+:12]([O-:14])=[O:13])[N:3]=1.[C:16]([O-])([O-])=O.[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:16][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:15])[C:8]=2[N+:12]([O-:14])=[O:13])[N:3]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 179891062-Chloro-6-methyl-5-nitroquinoline

生成物 1

HCID 7665652,6-Dimethyl-5-nitroquinoline収率 61.4%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
105 °C

実験手順

To a solution of 2-chloro-6-methyl-5-nitro-quinoline (350 mg, 1.57 mmol) in dioxane (6.7 mL) and water (0.7 mL) were added K2CO3 (652 mg, 4.72 mmol), trimethylboroxine (0.22 mL, 1.57 mmol) and PdCl2(dppf) (129 mg, 0.157 mmol) under Ar. The mixture was heated at 105° C. overnight, then cooled and the resulting solid was collected by filtration, washed with ethyl acetate, and dried. Purification by flash column (hexane/ethyl acetate gradient) gave 2,6-dimethyl-5-nitro-quinoline (195 mg, 61%).

後処理

  1. temperaturecooled
  2. filtrationthe resulting solid was collected by filtration
  3. washwashed with ethyl acetate
  4. customdried
  5. customPurification by flash column (hexane/ethyl acetate gradient)

出典と根拠

ORDレコード
ord-3eeba92cbac94ff5b6dcd2799c8dd6b2
出典データセット
uspto-grants-2013_05
特許番号
US08435990B2

関連ノート

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