Cesium carbonate → 4-[(4-Amino-3-nitrophenyl)oxy]-3-(methyloxy)benzaldehyde

HRID 547626Notes

Reaction equation

HRID 547626 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].F[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=1[O:21][CH3:22].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=2[O:21][CH3:22])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27373584-Fluoro-3-methoxybenzaldehydeHCID 37588824-Amino-3-Nitrophenol

Product 1

HCID 575858814-[(4-Amino-3-nitrophenyl)oxy]-3-(methyloxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Amino-3-nitrophenol (2 g, 13 mmol), 4-fluoro-3-(methyloxy)benzaldehyde (2 g, 13 mmol) and Cs2CO3 (5.1 g, 15.6 mmol) were stirred in dimethylformamide at 100 degrees Centigrade for approximately 18 hours. The reaction was filtered through an Alltech 75 mL Extract-Clean™ filter column packed with glass wool and eluted with ethyl acetate. The eluent was stirred with 5 mL of water then passed through a Varian Chem Elute™ 1010 column which was rinsed with 4-6 mL of ethyl acetate (gravity filtration). The eluent was dried over MgSO4, concentrated onto basic alumina and purified by silica gel column chromatography (hexanes/ethyl acetate gradient) to give 4-[(4-amino-3-nitrophenyl)oxy]-3-(methyloxy)benzaldehyde. (M+1) 289.0, 2.26 min (LC/MS method A)

Workup

  1. filtrationThe reaction was filtered through an Alltech 75 mL Extract-Clean™
  2. filtrationfilter column
  3. washeluted with ethyl acetate
  4. washElute™ 1010 column which
  5. washwas rinsed with 4-6 mL of ethyl acetate (gravity filtration)
  6. dry with materialThe eluent was dried over MgSO4
  7. concentrationconcentrated onto basic alumina
  8. custompurified by silica gel column chromatography (hexanes/ethyl acetate gradient)

Sources & evidence

ORD record
ord-078e34bb18ed4df7a9aae521bfb20e0a
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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