N-(5-Ethoxy-2-nitrophenyl)acetamide → 5-ethoxy-2-nitroaniline

HRID 1160632Notes

Reaction equation

HRID 1160632 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([N+:14]([O-:16])=[O:15])=[C:8]([NH:10]C(=O)C)[CH:9]=1)[CH3:2]>Cl.O>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([N+:14]([O-:16])=[O:15])=[C:8]([CH:9]=1)[NH2:10])[CH3:2]

Participants

4

Reactant 1

HCID 15322847N-(5-Ethoxy-2-nitrophenyl)acetamide

Product 1

HCID 51417895-ethoxy-2-nitroanilineYield 90.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A suspension of N-(5-ethoxy-2-nitrophenyl)acetamide (2.3 g, 10.3 mmol) in 5 M HCl (50 mL) was stirred at reflux temperature for 8 h. The resulting solution was cooled, diluted with water (200 mL), the resulting precipitate filtered and washed with water (2×10 mL) and dried to give aniline 15 (1.70 g, 90%) as an orange powder, mp (H2O) 101-102° C.; 1H NMR δ 8.06 (d, J=9.5 Hz, 1 H, H-3), 6.27 (dd, J=9.5, 2.6 Hz, 1 H, H-4), 6.13 (d, J=2.6 Hz, 1 H, H-6), 5.80 (br s, 2 H, NH2), 4.04 (q, J=7.0 Hz, 2 H, CH2O), 1.42 (t, J=7.0 Hz, 3 H, CH3); 13C NMR δ 164.8, 147.1, 128.4, 126.8, 106.9, 99.0, 64.1, 14.5. Anal. Calcd for C8H10N2O3: C, 52.7; H, 5.5; N, 15.4. Found: C, 52.6; H, 5.5; N, 15.4%.

Workup

  1. temperatureat reflux temperature for 8 h
  2. temperatureThe resulting solution was cooled
  3. filtrationthe resulting precipitate filtered
  4. washwashed with water (2×10 mL)
  5. customdried

Sources & evidence

ORD record
ord-8d3769460dcd43198fb2991ae2c5ccd4
Source dataset
uspto-grants-2010_10
Patent number
US07816521B2

Reaction notes

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