N-(2-ethyl-6-nitrophenyl)acetamide → 2-Ethyl-6-nitroaniline

HRID 471612Notes

Reaction equation

HRID 471612 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[NH:12]C(=O)C)[CH3:2]>CCO.Cl>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[NH2:12])[CH3:2]

Participants

4

Reactant 1

HCID 14147006N-(2-ethyl-6-nitrophenyl)acetamide

Product 1

HCID 224824552-Ethyl-6-nitroanilineYield 64.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of N-(2-ethyl-6-nitrophenyl)actamide (Example 139e) (0.62 g, 2.98 mmol) in EtOH (21 mL) and concentrated HCl (13 mL) was refluxed for 24 h. EtOH was evaporated, the residue was diluted with water (10 mL) and the pH was adjusted to pH˜8 with NaOH (2.0M aqueous solution). The neutralized solution was extracted with EtOAc (3×50 mL), the combined extract was washed with water and brine, and dried with anhydrous MgSO4. The filtrate was evaporated and the residue was purified on HPLC to give 0.32 g (64%) of 2-ethyl-6-nitroaniline as an orange solid. 1H NMR (400 MHz, DMSO-d6) δ 7.82-7.87 (m, 1H), 7.27-7.32 (m, 1H), 7.16 (broad s, 2H), 6.55-6.62 (m, 1H), 2.55 (q, J=7.2 Hz, 2H), 1.13 (t, J=7.2 Hz, 3H).

Workup

  1. customEtOH was evaporated
  2. additionthe residue was diluted with water (10 mL)
  3. extractionThe neutralized solution was extracted with EtOAc (3×50 mL)
  4. extractionthe combined extract
  5. washwas washed with water and brine
  6. dry with materialdried with anhydrous MgSO4
  7. customThe filtrate was evaporated
  8. customthe residue was purified on HPLC

Sources & evidence

ORD record
ord-5933c752a6954ce0bb9789a37019bb1d
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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