Nitric Acid → HCID 22477728, compound

HRID 2182402Notes

Reaction equation

HRID 2182402 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[CH:6][C:5]=1[CH2:14][CH3:15])[CH3:2].[N+:16]([O-])([OH:18])=[O:17]>C(OC(=O)C)(=O)C.C(O)(=O)C.O>[CH2:1]([O:3][C:4]1[C:5]([CH2:14][CH3:15])=[CH:6][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[C:8]([N+:16]([O-:18])=[O:17])[CH:9]=1)[CH3:2]

Participants

6

Reactant 2

HCID 944Nitric AcidHCID 20785076HCID 20785076, compound

Product 1

HCID 22477728HCID 22477728, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Procedure

N-(4-Ethoxy-3-ethyl-phenyl) acetamide [3.1 g, Reference Example 33(e)] was dissolved in acetic anhydride (5 mL), a solution of nitric acid in acetic acid (0.5 mL of 95% nitric acid, in 4 mL) was added and the mixture was stirred overnight at ambient temperature. The mixture was diluted with water (100 mL) and the aqueous mixture was extracted twice with ethyl acetate (100 mL). The combined extracts were evaporated and the residue was chromatographed on silica gel (heptane/ethyl acetate 9/1) to give N-(4-ethoxy-5-ethyl-2-nitrophenyl)acetamide (3.0 g) as a bright yellow solid. LC-MS (Method E): RT=3.27 minutes, 253 (M+H)+. (h) 1-Ethoxy-2-ethyl-4-nitrobenzene

Workup

  1. extractionthe aqueous mixture was extracted twice with ethyl acetate (100 mL)
  2. customThe combined extracts were evaporated
  3. customthe residue was chromatographed on silica gel (heptane/ethyl acetate 9/1)

Sources & evidence

ORD record
ord-42945b8eae85484c96b9b1d9eb2f143c
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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