Hydrazinium, 1,1,1-trimethyl-, iodide (1:1) → 2-Amino-4-cyano-3-hydroxynitrobenzene

HRID 751056

Reaction equation

HRID 751056 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[I-].C[N+:15](C)(C)N.CCC([O-])(C)C.[Na+]>CS(C)=O>[NH2:15][C:9]1[C:2]([OH:1])=[C:3]([CH:6]=[CH:7][C:8]=1[N+:10]([O-:12])=[O:11])[C:4]#[N:5]

Participants

5

Reactant 3

HCID 18683Hydrazinium, 1,1,1-trimethyl-, iodide (1:1)HCID 2861482-Hydroxy-4-nitrobenzonitrileHCID 2733478Sodium 2-methylbutan-2-olate

Product 1

HCID 218754622-Amino-4-cyano-3-hydroxynitrobenzeneYield 71.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-hydroxy-4-nitro-benzonitrile [1.0 g, 6.1 mmol, prepared as described in Yasubiro Imakura et. al. Chem. Pharm. Bull. 40 (7), 1691-1696 (1992)] in DMSO (60 mL) was added trimethylhydrazinium iodide (1.23 g, 6.09 mmol), followed by sodium tert-pentoxide (2.01 g, 6.09 mmol). The mixture was stirred at rt overnight, and then partitioned between 10% HCl and ether. The separated ether layer was washed with H2O, brine, dried (Na2SO4), and concentrated under reduced pressure to furnish the title compound (0.78 g) as a brown solid.

Workup

  1. custompartitioned between 10% HCl and ether
  2. washThe separated ether layer was washed with H2O, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e766a762834747b888294150cac2b1b3
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Linked notes

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