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

HRID 1870729노트

반응식

HRID 1870729 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 22135242(2-Aminophenyl)(3-methoxyphenyl)methanone수율 74%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9a8468b42af148ceb614fbf60629a576
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06100254

반응 노트

불러오는 중…