Acetic Acid → 3-Methoxy-4-(pyrimidin-2-yloxy)aniline

HRID 38245Notes

Reaction equation

HRID 38245 reaction equation
C(O)(=O)C.[CH3:5][O:6][C:7]1[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[CH:16][C:8]=1[O:9][C:10]1[N:15]=[CH:14][CH:13]=[CH:12][N:11]=1>O.CCO.[Fe]>[CH3:5][O:6][C:7]1[CH:19]=[C:18]([CH:17]=[CH:16][C:8]=1[O:9][C:10]1[N:11]=[CH:12][CH:13]=[CH:14][N:15]=1)[NH2:20]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 674400092-(2-Methoxy-4-nitrophenoxy)pyrimidine

Product 1

HCID 621109613-Methoxy-4-(pyrimidin-2-yloxy)anilineYield 100%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

According to Scheme 3 Step 2: A suspension of iron (4.45 mmol, 248 mg), acetic acid (1.07 mmol, 61 μL) and of 2-(2-methoxy-4-nitrophenoxy)pyrimidine (0.89 mmol, 220 mg) in water/EtOH (1:1, 7 mL) was stirred at 80° C. for 30 minutes. After evaporation of EtOH, the aqueous phase was basified with a saturated solution of NaHCO3 and was extracted with AcOEt. The organic phase was washed with brine, was dried over MgSO4, was filtered and was concentrated under reduced pressure to yield 3-methoxy-4-(pyrimidin-2-yloxy)aniline (0.89 mmol, 193 mg, 100%) as an oil. The product was used without further purification.

Workup

  1. customAfter evaporation of EtOH
  2. extractionwas extracted with AcOEt
  3. washThe organic phase was washed with brine
  4. dry with materialwas dried over MgSO4
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-755d5742c1bc446dbe64546a784b7ad0
Source dataset
uspto-grants-2013_09
Patent number
US08524726B2

Reaction notes

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