Hydrochloric Acid → 1-Chloro-3-methoxy-2-nitrobenzene

HRID 422316

반응식

HRID 422316 반응식
N([O-])=O.[Na+].[CH3:5][O:6][C:7]1[C:8]([N+:14]([O-:16])=[O:15])=[C:9](N)[CH:10]=[CH:11][CH:12]=1.C([O-])(O)=O.[Na+].[ClH:22]>O>[Cl:22][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([O:6][CH3:5])[C:8]=1[N+:14]([O-:16])=[O:15]

참가 물질

6

반응물 4

HCID 313Hydrochloric Acid2회HCID 516892Sodium BicarbonateHCID 104647003-Methoxy-2-nitroanilineHCID 23668193Sodium Nitrite

생성물 1

HCID 2322681-Chloro-3-methoxy-2-nitrobenzene수율 66%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of sodium nitrite (180 mg, 2.60 mmol) in water (0.5 mL) was added dropwise to a solution of 3-methoxy-2-nitro-phenylamine (400 mg, 2.38 mmol, Example 86(A)) in HCl (37%, 3.9 mL) at 0° C. over one hour period. Then the reaction mixture was added to a cold (0° C.) solution of CuCl2 (640 mg, 4.76 mmol) in HCl (6N, 3.5 mL). The resulting green solution was stirred at room temperature for 2 days. Then, the reaction mixture was poured onto ice and neutralized carefully with a saturated solution of NaHCO3. The aqueous phase was extracted with AcOEt. The resulting organic phase was washed with brine, dried over MgSO4, filtered and evaporated to yield 293 mg (1.56 mmol, 66%) of 1-chloro-3-methoxy-2-nitrobenzene as a brown oil.

후처리

  1. extractionThe aqueous phase was extracted with AcOEt
  2. washThe resulting organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-83fe41ffe4bf471989a904b2f4e16880
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101637B2

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