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

HRID 536228Notes

Reaction equation

HRID 536228 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].[OH-].[NH4+:16].II>C1COCC1>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:16])=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[O:13][CH3:14]

Participants

5

Reactant 3

HCID 807IodineHCID 14923Ammonium HydroxideHCID 96959Benzaldehyde, 4-hydroxy-3-methoxy-2-nitro-

Product 1

HCID 70592654-hydroxy-3-methoxy-2-nitrobenzonitrileYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Hydroxy-3-methoxy-2-nitrobenzaldehyde (200 g, 1.01 mol) was dissolved in THF (2.5 L) and then ammonium hydroxide (2.5 L) was added followed by iodine (464 g, 1.8 mol). The resulting mixture was allowed to stir for 2 days at which time it was concentrated under reduced pressure. The residue was acidified with HCl (2 N) and extracted into diethyl ether. The organic layer was washed with brine and dried (sodium sulfate) and concentrated under reduced pressure. The residue was washed with diethyl ether and dried under vacuum to provide the title compound (166 g, 84%): 1H NMR (DMSO-d6) δ: 11.91 (1H, s), 7.67 (1H, d), 7.20 (1H, d), 3.88 (3H, s)

Workup

  1. concentrationwas concentrated under reduced pressure
  2. extractionextracted into diethyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was washed with diethyl ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-041f6e276e7049b592989eb8f16fc7b0
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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