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

HRID 2088469

반응식

HRID 2088469 반응식
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

참가 물질

7

반응물 3

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

생성물 1

HCID 7665652,6-Dimethyl-5-nitroquinoline수율 61.4%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
105 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-3eeba92cbac94ff5b6dcd2799c8dd6b2
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08435990B2

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