2,6-Dichloro-3-nitrotoluene → 2,4-Dichloro-m-toluidine

HRID 348066

반응식

HRID 348066 반응식
Cl[Sn]Cl.O.[Cl:5][C:6]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[C:8]([Cl:15])[C:7]=1[CH3:16]>C(O)C>[Cl:5][C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8]([Cl:15])[C:7]=1[CH3:16]

참가 물질

4

반응물 2

HCID 971552,6-Dichloro-3-nitrotolueneHCID 43835034Tin dichloride dihydrate

생성물 1

HCID 882822,4-Dichloro-m-toluidine수율 99.4%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

To a solution of SnCl2.H2O (140 g, 0.62 mol) in ethanol (350 mL) was added a solution of 2,6-dichloro-3-nitrotoluene (25 g, 0.12 mol) in ethanol (50 mL). The reaction mixture was refluxed for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in water (100 mL), pH was adjusted to approximately pH 12 with 1N NaOH solution and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over sodium sulfate, and concentrated to afford 2,6-dichloro-3-aminotoluene (21 g, 98%); NMR (CDCl3) 2.42 (s, 3), 6.62 (d, 1), 7.14 (d, 1) ppm.

후처리

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water (100 mL)
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-059ce2e0c0144c7f816cb39769fdae6a
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176207B2

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