2-Chloro-3-nitrobenzamide → 2-Chloro-3-nitrobenzonitrile
Reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O>O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O([Si](C)(C)C)[Si](C)(C)C.ClCCCl>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]#[N:6]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of 2-chloro-3-nitrobenzamide (1.02 g, 4.9 mmol) in P2O5/(TMS)2O/1,2-dichloroethane (30 mL) was heated at 85° C. for 18 hours. After it was cooled to 25° C., the solution was filtered through a plug of silica gel (60 mL), eluting with 5% methanol/CHCl3 (400 mL). The combined washes were concentrated under reduced pressure to give 2-chloro-3-nitrobenzonitrile as an off-white solid (0.66 g, 74%).
Workup
- filtrationthe solution was filtered through a plug of silica gel (60 mL)
- washeluting with 5% methanol/CHCl3 (400 mL)
- concentrationThe combined washes were concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-04879d5591c84c1cb31861b2607d6a1f
- Source dataset
- uspto-grants-2002_02
- Patent number
- US06344459B1
Reaction notes
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