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

HRID 525984

反応式

HRID 525984 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-59e09aff113d4b98b0a32299a09ecac6
出典データセット
uspto-grants-2016_05
特許番号
US09343684B2

関連ノート

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