Hydrochloric Acid → N1-ethyl-3-nitrobenzene-1,4-diamine

HRID 1091659Notes

Reaction equation

HRID 1091659 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:16][CH3:17])C(=O)OC(C)(C)C)=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].Cl>O1CCOCC1>[CH2:16]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:18]([O-:20])=[O:19])[CH:4]=1)[CH3:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66593456Tert-butyl 4-amino-3-nitrophenyl(ethyl)carbamate

Product 1

HCID 19854182N1-ethyl-3-nitrobenzene-1,4-diamine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

The tert-butyl 4-amino-3-nitrophenyl(ethyl)carbamate from the previous step was dissolved in dioxane (35 mL) and hydrogen chloride (35 mL of a 4M solution in dioxane) was added. The mixture was stirred at room temperature for 18 hr and then the solvent was evaporated. The residue was dissolved in water (200 mL) and the solution adjusted to pH10 with 5M sodium hydroxide solution. The solution was extracted with EA (3×100 mL), and the combined EA extracts were washed with brine, dried over magnesium sulfate, and concentrated to give N1-ethyl-3-nitrobenzene-1,4-diamine as a purple solid (1.68 g).

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in water (200 mL)
  3. extractionThe solution was extracted with EA (3×100 mL)
  4. washthe combined EA extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b9c5afdc07d2455e8fec02adbbc2c1e0
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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