Ammonia → 4-hydroxy-3-methoxy-2-nitrobenzonitrile

HRID 1091519Notes

Reaction equation

HRID 1091519 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[O:13][CH3:14].II.[NH3:17]>O1CCCC1>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:17])=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[O:13][CH3:14]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 807IodineHCID 96959Benzaldehyde, 4-hydroxy-3-methoxy-2-nitro-

Product 1

HCID 70592654-hydroxy-3-methoxy-2-nitrobenzonitrileYield 84.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-hydroxy-3-methoxy-2-nitrobenzaldehyde 14.5 g (73.5 mmol) in 28% ammonia solution 150 mL and tetrahydrofuran 15 mL was added iodine 22.4 g (88.2 mmol) and stirred at room temperature for overnight. The reaction mixture was concentrated in vacuo. The residue was acidified with 2H HCl solution and extracted into diethyl ether. The organic layer was washed with brine, dried over MgSO4, filtrated and the solvent was evaporated. The residue was washed with diisopropyl ether to give the title compound 12.1 g as brown solid. Yield 84.5%

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionextracted into diethyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltrated
  6. customthe solvent was evaporated
  7. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-08548454e4c84dcf88c011ac1d8d61f4
Source dataset
uspto-grants-2012_03
Patent number
US08129386B2

Reaction notes

Loading…