Triethylamine → 4-Amino-2-chloro-3-fluorobenzonitrile
Reaction equation
Cl.NO.[NH2:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[C:7]([Cl:13])[C:6]=1[F:14].C([N:17](CC)CC)C.C1CCC(N=C=NC2CCCCC2)CC1>O.C(Cl)Cl.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].C(O)=O.N1C=CC=CC=1>[NH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:17])=[C:7]([Cl:13])[C:6]=1[F:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 5
Procedure
To a solution of hydroxylamine hydrochloride (336 mg, 4.84 mmol) in water (1.2 mL) was added 4-amino-2-chloro-3-fluorobenzaldehyde (73A) (0.800 g, 4.61 mmol) and pyridine (2.5 mL). After stirring at rt for 1 h, copper (II) sulfate pentahydrate (230 mg, 0.922 mmol) was added followed by a solution of triethylamine (1.40 mL, 9.68 mmol) in CH2Cl2 (2.5 mL). To the resulting dark green reaction mixture was then added a solution of DCC (1.14 g, 5.53 mmol) in CH2Cl2 (10 mL) and the reaction was stirred for 2 h. Formic acid (1 mL) was added and the reaction was stirred for 20 min, filtered through celite, and concentrated. The resulting residue was purified via silica gel chromatography eluting with 20-30% EtOAc/hexane to provide the title compound (0.780 g) as a light brown solid.
Workup
- stirringthe reaction was stirred for 2 h
- stirringthe reaction was stirred for 20 min
- filtrationfiltered through celite
- concentrationconcentrated
- customThe resulting residue was purified via silica gel chromatography
- washeluting with 20-30% EtOAc/hexane
Sources & evidence
- ORD record
- ord-fc9ae9e996d04c539de849d726f6718f
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07405234B2
Reaction notes
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