(4-Chloro-2-methyl-3-nitrophenoxy)acetonitrile → HCID 18789632, compound
Reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][C:8]#[N:9])=[C:4]([CH3:12])[C:3]=1[N+:13]([O-])=O>C(O)(=O)C.[Zn]>[NH2:13][C:3]1[C:4]([CH3:12])=[C:5]([CH:10]=[CH:11][C:2]=1[Cl:1])[O:6][CH2:7][C:8]#[N:9]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 62.5 °C
Procedure
A mixture of (4-chloro-2-methyl-3-nitrophenoxy)acetonitrile (9.1 g) and zinc (dust) (10.5 g) in glacial acetic acid (90 mL) was heated at 60-65° C. for 4 hr under an atmosphere of nitrogen. The reaction mixture was cooled to room temperature, then filtered through celite. The filtrate was evaporated under reduced pressure and the residue partitioned between ethyl ether (500 mL) and 10% ammonium hydroxide solution (500 mL). The ethereal solution was separated, washed with saturated sodium chloride solution, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue flash chromatographed on silica, eluting with ethyl acetate:hexane (1:4) to afford 4.76 g as a light yellow oil which crystallized on standing.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- filtrationfiltered through celite
- customThe filtrate was evaporated under reduced pressure
- customthe residue partitioned between ethyl ether (500 mL) and 10% ammonium hydroxide solution (500 mL)
- customThe ethereal solution was separated
- washwashed with saturated sodium chloride solution
- dry with materialdried over magnesium sulfate
- customThe solvent was removed under reduced pressure
- customthe residue flash chromatographed on silica
- washeluting with ethyl acetate:hexane (1:4)
- customto afford 4.76 g as a light yellow oil which
- customcrystallized
Sources & evidence
- ORD record
- ord-97dfbad5ce2749bb9231aff09858a9fa
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05952362
Reaction notes
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