4-Chloroaniline → N-(4-chlorophenyl)-5-nitronaphthalen-1-amine

HRID 1750872

反応式

HRID 1750872 の反応式
Br[C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>CC(N(C)C)=O.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:2]2[C:11]3[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4][CH:3]=2)=[CH:18][CH:17]=1

参加物

7

反応物 3

HCID 78124-ChloroanilineHCID 2199881-Bromo-5-nitronaphthaleneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

生成物 1

HCID 101043238N-(4-chlorophenyl)-5-nitronaphthalen-1-amine収率 66%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
140 °C

実験手順

1-bromo-5-nitronaphthalene (131 mg, 0.52 mmol) was dissolved in DMA (5 mL), and added with 4-chloroaniline (60 mg, 0.47 mmol), Xantphos (27 mg, 0.047 mmol), Pd2(dba)3 (17.2 mg, 0.019 mmol) and CsCO3 (306 mg, 0.94 mmol) at room temperature. The reaction solution was sealed and stirred for about 3 hours under microwave conditions at 140° C. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and washed with a saturated aqueous solution of sodium bicarbonate and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrated compound purified using silica gel chromatography (ethyl acetate:hexane=1:5 (v/v)) to obtain the title compound (92 mg, 66%).

後処理

  1. customThe reaction solution was sealed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washwashed with a saturated aqueous solution of sodium bicarbonate and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe concentrated compound purified

出典と根拠

ORDレコード
ord-007c4a144d4f44dbac7d13bd595265a8
出典データセット
uspto-grants-2015_10
特許番号
US09156852B2

関連ノート

読み込み中…