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

HRID 1189117

Reaction equation

HRID 1189117 reaction equation
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]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 516892Sodium BicarbonateHCID 104647003-Methoxy-2-nitroanilineHCID 23668193Sodium Nitrite

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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 (6 N, 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.

Workup

  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

Sources & evidence

ORD record
ord-53639f7f68314d5bb41c31e27a594ef8
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Linked notes

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