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

HRID 711749Notes

Reaction equation

HRID 711749 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-a5c152e2fa6e44139bde8ae9cb003814
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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