Nitric Acid → N-(4-ethyl-2-nitrophenyl)acetamide

HRID 2182401Notes

Reaction equation

HRID 2182401 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][C:6]([NH:7][C:8](=[O:10])[CH3:9])=[CH:5][CH:4]=1)[CH3:2].[N+:13]([O-])([OH:15])=[O:14]>C(OC(=O)C)(=O)C.C(O)(=O)C>[CH2:1]([C:3]1[CH:12]=[CH:11][C:6]([NH:7][C:8](=[O:10])[CH3:9])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 72893N-(4-Ethylphenyl)acetamide

Product 1

HCID 15919553N-(4-ethyl-2-nitrophenyl)acetamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 4-ethyl-N-acetyl-aniline [3 g, Reference Example 33(a)] in acetic anhydride (8 mL) and acetic acid (4 mL), at −5° C., was treated dropwise with a mixture of acetic acid (1.75 mL) and concentrated nitric acid (1.22 mL). The mixture was warmed to 0° C., then stirred at 0° C. for 2 hours and then poured onto water. This mixture was evaporated and the resulting oil was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate and then evaporated. The residual oil was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and petroleum ether (2:5) to give 4-ethyl-2-nitro-N-acetyl-aniline (1.4 g) as an orange solid. LC-MS (METHOD B): RT=2.95 minutes; 209.2 (M+H)+. (b) 4-Ethyl-5-methyl-2-nitro-N-acetyl-aniline

Workup

  1. additionpoured onto water
  2. customThis mixture was evaporated
  3. customthe resulting oil was partitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated
  6. additionThe residual oil was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and petroleum ether (2:5)

Sources & evidence

ORD record
ord-ef538837378842ff8f445f1b32dd9dab
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

Loading…