Hydrochloric Acid → (2-Aminophenyl)(3-methoxyphenyl)methanone

HRID 1870729ノート

反応式

HRID 1870729 の反応式
O(N(C)[C:4](=[O:12])[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH2:7])C.Br[C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1N)[O:18][CH3:19].[Li]CCCC.Cl>C1COCC1>[NH2:7][C:6]1[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=1[C:4]([C:15]1[CH:22]=[CH:21][CH:20]=[C:17]([O:18][CH3:19])[CH:16]=1)=[O:12]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 108996712-Bromo-4-methoxyanilineHCID 110522422-amino-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

生成物 1

HCID 22135242(2-Aminophenyl)(3-methoxyphenyl)methanone収率 74%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

In a flame-dried round bottom flask, anthranilic acid N-methoxyl-N-methylamide (8.00 g, 44.4 mmol) and m-bromoanisidine (8.31 g, 44.4 g) were dissolved in 250 mL of THF and the resulting solution was cooled to -78° C. With vigorous stirring, 2 equiv of nBuLi in hexanes (55.5 mL, 1.6 M, 88.8 mmol) was added dropwise by a syringe pump at 0.6 mL/min. After 20 min, 80 mL of 1 N hydrochloric acid was carefully added, the mixture was extracted with ethyl acetate (600 mL), and the ethyl acetate was washed with water (300 mL) and brine (300 mL), dried over sodium sulfate and concentrated in vacuo. Flash chromatography with 95:5 hexanes/ethyl acetate afforded 6.92 g (69% yield) of 2-amino-3'-methoxybenzophenone as a yellow oil. 2-Amino-3'-methoxybenzophenone was converted to 2-amino-3'-hydroxybenzophenone (below) prior to characterization.

後処理

  1. extractionthe mixture was extracted with ethyl acetate (600 mL)
  2. washthe ethyl acetate was washed with water (300 mL) and brine (300 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-9a8468b42af148ceb614fbf60629a576
出典データセット
uspto-grants-2000_08
特許番号
US06100254

反応ノート

読み込み中…