2-(Ethanesulfonyl)-5-nitrobenzonitrile → 5-Amino-2-(ethanesulfonyl)benzonitrile

HRID 735502Notes

Reaction equation

HRID 735502 reaction equation
[CH2:1]([S:3]([C:6]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:7]=1[C:8]#[N:9])(=[O:5])=[O:4])[CH3:2]>CO.[Pd]>[NH2:14][C:11]1[CH:12]=[CH:13][C:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[C:7]([CH:10]=1)[C:8]#[N:9]

Participants

4

Reactant 1

HCID 574481822-(Ethanesulfonyl)-5-nitrobenzonitrile

Product 1

HCID 598380375-Amino-2-(ethanesulfonyl)benzonitrileYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 6A (0.554 g, 2.31 mmol) in MeOH (60 mL) was hydrogenated (60 psi) over 10% palladium on carbon (99 mg) for 3 h at rt. The reaction mixture was filtered and concentrated under reduced pressure to give 6B (464 mg, 96%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 1.30 (t, J=7.25 Hz, 3H), 3.30 (q, J=7.47 Hz, 2H), 4.62 (s, 2H), 6.89 (dd, J=8.79, 2.64 Hz, 1H), 7.04 (d, J=2.20 Hz, 1H), 7.83 (d, J=8.79 Hz, 1H).

Workup

  1. customfor 3 h
  2. customat rt
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fce27077a3e94e2cbca9b2251bffc956
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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