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

HRID 1259512Notes

Reaction equation

HRID 1259512 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-nitrobenzonitrile

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).

Sources & evidence

ORD record
ord-a638210d2e6c4c1296028b718b48653d
Source dataset
uspto-grants-2013_06
Patent number
US08466283B2

Reaction notes

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