Potassium Carbonate → 1-(2-Amino-3-nitrophenoxy)-2,3-epoxypropane

HRID 896007Notes

Reaction equation

HRID 896007 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[CH2:12]([CH:14]1[O:16][CH2:15]1)Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:8]([C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([O:11][CH2:12][CH:14]2[CH2:15][O:16]2)[C:2]=1[NH2:1])([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 113448381-(2-Amino-3-nitrophenoxy)-2,3-epoxypropaneYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 2-amino-3-nitro-phenol (18.0 g, 0.117 mol) and epibromohydrin (21.0 g, 0.15 mol) in DMF (200 mL) containing potassium carbonate (20.7 g, 0.15 mol) was stirred at 70° C. overnight. The mixture was evaporated in vacuo, water was added to the residue and the mixture was then extracted with dichloromethane (2×300 mL), the combined organic layers were washed with saturated sodium chloride (300 mL), dried and concentrated. Purification by flash column chromatography (silica gel, methylene chloride) provided 15.0 g of the title compound as an orange solid. 1H NMR (DMSO-d6): δ 7.60 (dd, 1H); 7.11 (dd, 1H); 7.05 (s, 2H); 6.60 (dd, 1H); 4.40 (dd, 1H); 3.93 (dd, 1H); 3.42 (m, 1H); 2.87 (dd, 1H); 2.75 (dd, 1H).

Workup

  1. customThe mixture was evaporated in vacuo, water
  2. additionwas added to the residue
  3. extractionthe mixture was then extracted with dichloromethane (2×300 mL)
  4. washthe combined organic layers were washed with saturated sodium chloride (300 mL)
  5. customdried
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (silica gel, methylene chloride)

Sources & evidence

ORD record
ord-17a455429cd94a4aa2dc136f98415035
Source dataset
uspto-grants-2005_07
Patent number
US06919334B2

Reaction notes

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