Phenyl-1-naphthylamine → N-(4-methoxyphenyl)-N-phenylnaphthalen-1-amine

HRID 525984

반응식

HRID 525984 반응식
[C:1]1([NH:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C=O)C.[Cu]>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)=[CH:20][CH:21]=1

참가 물질

7

반응물 4

HCID 7013Phenyl-1-naphthylamineHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 696764-Iodoanisole

생성물 1

HCID 22973981N-(4-methoxyphenyl)-N-phenylnaphthalen-1-amine수율 35%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 6228Dimethylformamide용매

실험 절차

A mixture of N-phenylnaphthalen-1-amine (5.0 g, 22.8 mmol), 4-iodoanisole (8.0 g, 34.2 mmol), copper powder (2.89 g, 45.6 mmol), K2CO3 (12.59 g, 91.2 mmol) and 18-crown-6 (0.607 g, 2.3 mmol) in DMF (200 mL) was degassed and heated to reflux for overnight under argon. After the salt and copper were filtered off, the solution was poured into water (300 mL), and extracted with DCM (2×300 mL). The organic phase was combined and washed with brine, dried over Na2SO4, loaded on silica gel, purified by flash column (5 to 20% DCM in hexanes). The desired fraction was collected, concentrated, and recrystallized in ethyl acetate/methanol to obtain a white solid (Compound 5) (2.59 g, in 35% yield).

후처리

  1. customwas degassed
  2. temperatureheated
  3. temperatureto reflux for overnight under argon
  4. filtrationAfter the salt and copper were filtered off
  5. additionthe solution was poured into water (300 mL)
  6. extractionextracted with DCM (2×300 mL)
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. custompurified by flash column (5 to 20% DCM in hexanes)
  10. customThe desired fraction was collected
  11. concentrationconcentrated
  12. customrecrystallized in ethyl acetate/methanol

출처 및 근거

ORD 기록
ord-59e09aff113d4b98b0a32299a09ecac6
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09343684B2

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