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

HRID 842927

反応式

HRID 842927 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 3437964,5-Dichloro-2-methylaniline収率 56.1%

試薬・触媒・溶媒 1

HCID 10313229titanium(III) trichloride溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b3fff543e149441391bab4be31b9db1a
出典データセット
uspto-grants-2002_04
特許番号
US06376530B1

関連ノート

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