Water → 3-Nitrobenzonitrile

HRID 1370109Notes

Reaction equation

HRID 1370109 reaction equation
OCC(N[C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[N+:15]([O-:17])=[O:16])CO.COC(OC)(C)C.O>ClCCl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[N+:15]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:7]=1)[C:11]#[N:12])([O-:17])=[O:16]

Participants

6

Reactant 3

HCID 962WaterHCID 64952,2-DimethoxypropaneHCID 18509808HCID 18509808, compound

Product 1

HCID 120793-NitrobenzonitrileYield 154.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[2-hydroxy-1-(hydroxymethyl)ethylamino]-3-nitrobenzonitrile (1.35 g), 2,2-dimethoxypropane (1.4 g) and p-toluenesulfonic acid (10 mg) in anhydrous dichloromethane (30 mL) was stirred at ambient temperature for 8 hours. The mixture was poured into water and extracted with chloroform. The organic layer was washed with brine and dried over magnesium sulfate. After evaporation of the solvent, the residue was triturated with diethyl ether to give 4-[(2,2-dimethyl-1,3-dioxan-5-yl)amino[-3-nitrobenzonitrile (1.3 g) as yellow powders.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of the solvent
  5. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-bac17fe5bf344159bfe8f4b7564c6bb7
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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