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

HRID 929096

반응식

HRID 929096 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

HCID 152786073-Chloro-2,4-dimethylaniline

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매HCID 962Water용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-41322738a4704d7da06d7072ea555f4f
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290503B2

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