Nitrogen → 2-Chloro-N-(3-nitrophenyl)pyridine-4-amine
Reaction equation
N#N.[Cl:3][C:4]1[CH:9]=[C:8](I)[CH:7]=[CH:6][N:5]=1.[N+:11]([C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17])([O-:13])=[O:12].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:3][C:4]1[CH:9]=[C:8]([NH:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:14]([N+:11]([O-:13])=[O:12])[CH:15]=2)[CH:7]=[CH:6][N:5]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
To a degassed (15 min, N2) suspension of 2-chloro-4-iodopyridine (3.0 g, 12.53 mmol), 3-nitroaniline (1.82 g, 13.18 mmol), BINAP (0.39 g, 0.626 mmol) and Cs2CO3 (8.16 g, 25.04 mmol) in toluene (72 mL) was added Pd(OAc)2 (0.084 g, 0.374 mmol). The reaction tube was sealed and the mixture stirred at 90° C. for 18 h. The mixture was cooled to rt and filtered, washing with EtOAc. The orange/yellow solid collected was washed with CH2Cl2 until all the product washed through into the filtrate. The filtrate was concentrated to afford 2-Chloro-N-(3-nitrophenyl)pyridine-4-amine as a bright yellow solid. Additional product was collected from the solid collected upon concentration of the previous filtrate, after washing with CH2Cl2. No further purification. Total amount of product collected was 2.85 g (91% yield).
Workup
- customTo a degassed
- customThe reaction tube was sealed
- temperatureThe mixture was cooled to rt
- filtrationfiltered
- washwashing with EtOAc
- customThe orange/yellow solid collected
- washwas washed with CH2Cl2 until all the product
- washwashed through into the filtrate
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-c47aed5d9bd24fecaae32a9bb177869a
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09328103B2
Reaction notes
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