4-(Ethylamino)-3-nitrobenzonitrile → 3-Amino-4-(ethylamino)benzonitrile

HRID 600820Notes

Reaction equation

HRID 600820 reaction equation
[CH2:1]([NH:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[N+:12]([O-])=O)[CH3:2]>[Pd].CCOC(C)=O>[NH2:12][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:4]=1[NH:3][CH2:1][CH3:2])[C:8]#[N:9]

Participants

4

Reactant 1

HCID 31180704-(Ethylamino)-3-nitrobenzonitrile

Product 1

HCID 38462923-Amino-4-(ethylamino)benzonitrileYield 102.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 250 mL pressure flask was sparged with a stream of nitrogen and then charged with 4-ethylamino-3-nitrobenzonitrile (1.6 g, 8.5 mmol), EtOAc (35 mL) and 10% w/w Pd/C (1.0 g, 11 mol %). The pressure flask was affixed to a Parr hydrogenation apparatus, evacuated briefly and backfilled with argon (2 cycles), then evacuated briefly and backfilled with hydrogen (3 cycles). The flask was pressurized to 50 psi of hydrogen and shaken vigorously. After 3 h, the flask was vented and sparged with a stream of nitrogen for 5 min. The reaction mixture was filtered through Celite and concentrated under reduced pressure to give the title product (1.4 g, quant.) as a pale brown solid. 1H-NMR (CDCl3): δ 7.14 (1H, dd), 6.91 (1H, d), 6.56 (1H, d), 3.91 (1H, br s), 3.32 (2H, br s), 3.19 (2H, q), 1.31 (3H, t).

Workup

  1. customA 250 mL pressure flask was sparged with a stream of nitrogen
  2. customevacuated briefly
  3. customevacuated briefly
  4. customsparged with a stream of nitrogen for 5 min
  5. filtrationThe reaction mixture was filtered through Celite
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e8de926f57d447d497f57bf13eebf468
Source dataset
uspto-grants-2011_03
Patent number
US07902237B2

Reaction notes

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