Aniline → 2-Aminophenyl-4-nitro-benzonitrile

HRID 1609855

反応式

HRID 1609855 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 179479572-Aminophenyl-4-nitro-benzonitrile収率 88.4%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5a79adfa8994446aaeb07317d99fe9e9
出典データセット
uspto-grants-2006_01
特許番号
US06982270B1

関連ノート

読み込み中…