Acetic Anhydride → HCID 21192579, compound

HRID 1067950Notes

Reaction equation

HRID 1067950 reaction equation
[CH2:1]([N:3]([CH2:13][CH2:14][OH:15])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)[CH3:2].[C:16](OC(=O)C)(=[O:18])[CH3:17].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.C(OCC)(=O)C>[C:16]([O:15][CH2:14][CH2:13][N:3]([CH2:1][CH3:2])[C:4]1[CH:5]=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=1)(=[O:18])[CH3:17]

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 13797249HCID 13797249, compound

Product 1

HCID 21192579HCID 21192579, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a flask containing 2-(ethyl-4-nitroanilino)-1-ethanol (4.2 g) and 4-dimethylaminopyridine (0.12 g) in pyridine (20 mL) at 0° C. under a drying tube is added acetic anhydride (5.0 mL) dropwise. The reaction mixture is allowed to warm to room temperature overnight. The reaction mixture is diluted with ethyl acetate and partioned against saturated aqueous sodium carbonate. The layers are separated and the aqueous phase extracted with two additional portions of ethyl acetate. The combined organic phases are washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue is azeotroped three times with toluene to remove residual pyridine. The residue is adsorbed onto silica and chromatographed on silica eluting with 50% ethyl acetate in heptane. The product-containing fractions are evaporated to give 4.9 g of 2-(ethyl-4-nitroanilino)ethyl acetate as a yellow oil.

Workup

  1. customThe layers are separated
  2. extractionthe aqueous phase extracted with two additional portions of ethyl acetate
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is azeotroped three times with toluene
  7. customto remove residual pyridine
  8. customchromatographed on silica eluting with 50% ethyl acetate in heptane
  9. customThe product-containing fractions are evaporated

Sources & evidence

ORD record
ord-16be2219641046788b2d504de124f42d
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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