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

HRID 1787540Notes

Reaction equation

HRID 1787540 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-b4b002b1a6e74f6bb069ddbb27eaedff
Source dataset
uspto-grants-2009_03
Patent number
US07511041B2

Reaction notes

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