Ethylene Glycol → 4-{[4-(1,3-Dioxolan-2-yl)-2-(methyloxy)phenyl]oxy}-2-nitroaniline

HRID 547627Notes

Reaction equation

HRID 547627 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=2[O:17][CH3:18])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].[CH2:22](O)[CH2:23][OH:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[O:14]1[CH2:22][CH2:23][O:24][CH:13]1[C:12]1[CH:15]=[CH:16][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:19]([O-:21])=[O:20])[CH:4]=2)=[C:10]([O:17][CH3:18])[CH:11]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 575858814-[(4-Amino-3-nitrophenyl)oxy]-3-(methyloxy)benzaldehyde

Product 1

HCID 575859654-{[4-(1,3-Dioxolan-2-yl)-2-(methyloxy)phenyl]oxy}-2-nitroaniline

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[(4-amino-3-nitrophenyl)oxy]-3-(methyloxy)benzaldehyde (2.42 g, 8.4 mmol), ethyleneglycol (4 ml) and p-toluenesulfonic acid (50 mg) in 50 mL of toluene was heated at 125 degrees Centigrade with a Dean-Stark trap for approximately 18 hours. The reaction mixture was diluted with ethyl acetate and washed twice with saturated NaHCO3. The aqueous layers were extracted with ethyl acetate. The organic layers were combined, dried over MgSO4 and concentrated to give 4-{[4-(1,3-dioxolan-2-yl)-2-(methyloxy) phenyl]oxy}-2-nitroaniline. (M+1) 332.9, 2.13 min (LC/MS method B)

Workup

  1. washwashed twice with saturated NaHCO3
  2. extractionThe aqueous layers were extracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-734c4a7a7a9a432ca7bdeb577a62e350
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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