Water → 2-Amino-4-methoxybenzamide

HRID 617120

반응식

HRID 617120 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[N+:11]([O-])=O)#[N:2].O.O.[Sn](Cl)Cl.C(=O)(O)[O-:20].[Na+].O>C(O)C>[NH2:11][C:4]1[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=1[C:1]([NH2:2])=[O:20]

참가 물질

6

반응물 4

HCID 962WaterHCID 61436Stannous chloride dihydrateHCID 2886654-Methoxy-2-nitrobenzonitrileHCID 516892Sodium Bicarbonate

생성물 1

HCID 140230022-Amino-4-methoxybenzamide

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 37.4 g (0.210 mol) of 4-cyano-3-nitroanisole in 500 mL of ethanol was added 221.6 g (0.982 mol) of tin(II) chloride dihydrate. The reaction mixture was stirred and heated under reflux for 1 hour. After cooling to room temperature, the reaction mixture was poured onto ice. Aqueous sodium bicarbonate was added slowly to the ice mixture until the solution reached pH 7-8. Additional water was added to the mixture, which was then extracted with methylene chloride (2×400 mL) and ethyl acetate (1×300 mL). The separated aqueous layers were filtered between each of the extractions. The off white residue collected on the filters was rinsed with methylene chloride and ethyl acetate several times. The combined organic phases were then dried over magnesium sulfate, filtered and evaporated in the rotary evaporator to obtain 28.5 g crude product (mp 154-155° C.).

후처리

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. additionthe reaction mixture was poured onto ice
  4. extractionwas then extracted with methylene chloride (2×400 mL) and ethyl acetate (1×300 mL)
  5. filtrationThe separated aqueous layers were filtered between each
  6. extractionof the extractions
  7. customThe off white residue collected on the filters
  8. washwas rinsed with methylene chloride and ethyl acetate several times
  9. dry with materialThe combined organic phases were then dried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated in the rotary evaporator

출처 및 근거

ORD 기록
ord-429fdaa3cb4b416089a9922024c196f2
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05948775

연결된 노트

불러오는 중…