4-Hydroxybenzaldehyde → HCID 57585954, compound

HRID 547639Notes

Reaction equation

HRID 547639 reaction equation
[F:1][C:2]1[C:8](F)=[C:7]([F:10])[CH:6]=[C:5]([N+:11]([O-:13])=[O:12])[C:3]=1[NH2:4].[OH:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[NH2:4][C:3]1[C:2]([F:1])=[C:8]([O:14][C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=2)[C:7]([F:10])=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 10796Cesium carbonateHCID 27757632,3,4-Trifluoro-6-nitroaniline

Product 1

HCID 57585954HCID 57585954, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,3,4-Trifluoro-6-nitroaniline (5 g, 26 mmol), 4-hydroxybenzaldehyde (3.5 g, 28.6 mmol) and Cs2CO3 (10.5 g, 32.6 mmol) were stirred in 150 mL of dimethylformamide at 65 degrees Centigrade for approximately 18 hours. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate and water. The aqueous layer was extracted three times with ethyl acetate. The organic layers were combined, washed five times with brine, dried over Mg2SO4 and concentrated onto basic alumina. The residue was purified by silica gel column chromatography (hexane to ethyl acetate gradient) to give 4-[(3-amino-2,6-difluoro-4-nitrophenyl)oxy]benzaldehyde. 1H NMR (400 MHz, DMSO-d6) delta ppm 7.29 (d, J=8.8 Hz, 2 H) 7.46 (s., 2 H) 7.93 (d, J=8.8 Hz, 2 H) 7.98 (dd, J=11.0, 1.7 Hz, 1 H) 9.93 (s., 1 H)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. extractionThe aqueous layer was extracted three times with ethyl acetate
  4. washwashed five times with brine
  5. dry with materialdried over Mg2SO4
  6. concentrationconcentrated onto basic alumina
  7. customThe residue was purified by silica gel column chromatography (hexane to ethyl acetate gradient)

Sources & evidence

ORD record
ord-4ee21fc59436496aa437617d43e78908
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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