Hydrochloric Acid → (2-Amino-4-methoxyphenyl)(phenyl)methanone

HRID 1497262노트

반응식

HRID 1497262 반응식
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:9][C:10]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:11]=1[C:12]#N.Cl.[OH-:21].[Na+]>C(OCC)C>[NH2:9][C:10]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:11]=1[C:12]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:21]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 37231282-Amino-4-methoxybenzonitrileHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 254180(2-Amino-4-methoxyphenyl)(phenyl)methanone수율 85%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
0 °C

실험 절차

A solution of phenylmagnesium bromide (6.75 ml, 3M solution in diethyl ether, 20.2 mmol) in diethyl ether (15 ml) was added dropwise to a solution of 2-amino-4-methoxybenzonitrile (1000 mg, 6.75 mmol) in diethyl ether (20 ml) at 0° C. The resulting suspension was heated to reflux for 2 h. The mixture was then cooled to 0° C. and 2N HCl (40 ml) was added very carefully. After complete addition, the mixture was heated to 55° C. for 2 h. Then 3N NaOH (˜20 ml) was added at 0° C. to adjust the pH to 9. The mixture was extracted with EtOAc and the combined organic extracts were washed with brine, dried with Na2SO4 and evaporated. The remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 85:15-70:30) to afford the title compound (1300 mg, 85%) as yellow solid. MS (ESI): 228.4 (M+H)+.

후처리

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux for 2 h
  3. additionAfter complete addition
  4. temperaturethe mixture was heated to 55° C. for 2 h
  5. extractionThe mixture was extracted with EtOAc
  6. washthe combined organic extracts were washed with brine
  7. dry with materialdried with Na2SO4
  8. customevaporated
  9. customThe remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 85:15-70:30)

출처 및 근거

ORD 기록
ord-58c601a713444577a22c8962b6f28117
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199938B2

반응 노트

불러오는 중…