4-[(3-Hydroxypropyl)amino]-3-nitrobenzonitrile → HCID 22349277, compound

HRID 590407Notes

Reaction equation

HRID 590407 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[N+:14]([O-])=O>CCO>[NH2:14][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:6]=1[NH:5][CH2:4][CH2:3][CH2:2][OH:1])[C:10]#[N:11]

Participants

3

Reactant 1

HCID 223493164-[(3-Hydroxypropyl)amino]-3-nitrobenzonitrile2×

Product 1

HCID 22349277HCID 22349277, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 4-[(3-hydroxypropyl)amino]-3-nitrobenzonitrile (Intermediate 95, 13.4 g, 0.06 mol) in EtOH (500 mL) was added, under argon atmosphere, palladium over carbon (350 mg, 3.3 mmol of a 10% Pd/C) and the mixture was degassed. Then, H2 was added up to an internal pressure of 20 psi, and the final suspension was stirred at room temperature for 2.5 hours. The crude was filtered through a Whatmann glass micro fibre filter and the solvent was removed under reduced pressure to afford the title compound as a brownish solid (11.5 g, 95% yield) which was used in the next step without further purification.

Workup

  1. additionwas added, under argon atmosphere
  2. custompalladium over carbon (350 mg, 3.3 mmol of a 10% Pd/C) and the mixture was degassed
  3. additionThen, H2 was added up to an internal pressure of 20 psi
  4. filtrationThe crude was filtered through a Whatmann glass micro fibre
  5. filtrationfilter
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2dc2b9ecc0384d7f9da2111b2f260d93
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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