Sodium Hydroxide → 4,5-Dichloro-2-methylaniline

HRID 842927

반응식

HRID 842927 반응식
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N+:9]([O-])=O)=[C:4]([CH3:12])[CH:3]=1.[OH-].[Na+]>[Cl-].[Cl-].[Cl-].[Ti+3]>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([CH3:12])[CH:3]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 3437951,2-Dichloro-4-methyl-5-nitrobenzene

생성물 1

HCID 3437964,5-Dichloro-2-methylaniline수율 56.1%

시약·촉매·용매 1

HCID 10313229titanium(III) trichloride용매

실험 절차

4,5-Dichloro-2-methyl-nitrobenzene 5 (5.0 g, 24.3 mmol) was heated at 100° C. in titanium trichloride (30% in aqueous hdyrochloric acid, 25 mL) for 2 hrs., cooled to RT, the reaction solution was basified to pH 8 with 50% aqueous sodium hydroxide, then extracted with ethyl acetate. The ethyl acetate layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography using 10% ethyl acetate in hexanes to give 2.4 g (56%) of the title product. 1H NMR (400 MHz, CDCl3) δ7.09 (s, 1 H, Ar), 6.74 (s , 1 H, Ar), 3.63 (s, 2 H, NH2), 2.10 (s, 3H, CH3).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-b3fff543e149441391bab4be31b9db1a
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06376530B1

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