Sodium Hydroxide → 3-Chloro-2,4-dimethylaniline

HRID 2361152ノート

反応式

HRID 2361152 の反応式
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH3:12].ClC1C(C)=CC([N+]([O-])=O)=CC=1C.Cl[Sn]Cl.[OH-].[Na+]>CCO.Cl.O>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([CH:5]=[CH:4][C:3]=1[CH3:12])[NH2:9]

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 99205692-Chloro-1,3-dimethyl-5-nitrobenzeneHCID 213963312-Chloro-1,3-dimethyl-4-nitrobenzene

生成物 1

HCID 152786073-Chloro-2,4-dimethylaniline

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a solution of a mixture 2-chloro-1,3-dimethyl-4-nitro-benzene and chloro-1,3-dimethyl-5-nitro-benzene (12.8 g, 69 mmol) in EtOH (75 mL), conc. HCl (75 mL) was added. Than SnCl2 (51.0 g) was added in two portions. The mixture was stirred overnight at RT, then heated at 60° C. for 30 min, cooled to 0-5° C. (ice bath). Neutralized with NaOH (70 g) in H2O (500 ml). The product was extracted with Et2O (500 ml). Extract was dried over Na2SO4, evaporated. The residue was crystallized two times from hexane providing 3.66 g 3-chloro-2,4-dimethyl-phenylamine as white crystals. The filtrates were evaporated in vacuo and the residue was separated on SiO2 column (200 g), hexane-EtOAc (0 to 10% v/v). providing additionally 3.11 g of the product. Yield 6.77 g (43.5 mmol, 63%).

後処理

  1. temperatureheated at 60° C. for 30 min
  2. temperaturecooled to 0-5° C. (ice bath)
  3. extractionThe product was extracted with Et2O (500 ml)
  4. extractionExtract
  5. dry with materialwas dried over Na2SO4
  6. customevaporated
  7. customThe residue was crystallized two times from hexane providing 3.66 g 3-chloro-2,4-dimethyl-phenylamine as white crystals
  8. customThe filtrates were evaporated in vacuo
  9. customthe residue was separated on SiO2 column (200 g), hexane-EtOAc (0 to 10% v/v)

出典と根拠

ORDレコード
ord-e8f983e816cc44a3bb039f62054fdadf
出典データセット
uspto-grants-2014_04
特許番号
US08686005B2

反応ノート

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