Aniline → 2-Aminophenyl-4-nitro-benzonitrile

HRID 1609855

반응식

HRID 1609855 반응식
Cl[C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CN1CCCC1=O.C(N(C(C)C)CC)(C)C>CCOC(C)=O>[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

참가 물질

6

반응물 4

HCID 6115AnilineHCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 1414012-Chloro-4-nitrobenzonitrile

생성물 1

HCID 179479572-Aminophenyl-4-nitro-benzonitrile수율 88.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

2-Chloro-4-nitro-benzonitrile (Aldrich) (3.64 g, 20 mmol), aniline (2 mL, 22 mmol), 1-methyl-2-pyrollidinone (10 mL) and diisopropylethylamine (4 mL) were combined and heated to 120° under Ar for 18 h, cooler poured into EtOAc (150 mL), washed with H20 (3×50 mL) and satd aq NaCl (50 mL), dried (Na2SO4), concentrated, and the residue was triturated with hexane, filtered and the solid was washed with hexane and dried in vacuo to afford 4.23 g (88%) of the title compound as a light green solid. 1H NMR (400) MHz, δ: 8.45 (finely split doublet, 1), 8.19 (dd, 1), 7.48 (m,3), 7.28 (d,2), 7.06 (d,1), 6.96 (br s,1).

후처리

  1. temperatureheated to 120° under Ar for 18 h
  2. washwashed with H20 (3×50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customthe residue was triturated with hexane
  6. filtrationfiltered
  7. washthe solid was washed with hexane
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-5a79adfa8994446aaeb07317d99fe9e9
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982270B1

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