Pyridine → HCID 3323861, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].N1C=CC=CC=1.[Cl:18][C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([Cl:28])[CH:27]=1)[C:22](Cl)=[O:23]>ClCCl>[Cl:18][C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([Cl:28])[CH:27]=1)[C:22]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)=[O:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4-fluoro-3-nitro-phenylamine (3.0 g, 20 mmol) in dichloromethane (60 mL) was added pyridine (3.2 g, 40.0 mmol). The solution was cooled to 0° C. and 3,5-dichlorobenzoyl chloride (4.0 g, 20.0 mmol) was added. The ice bath was removed and the reaction was allowed to warm to room temperature over 18 h. The reaction was poured into water and a precipitate formed. The solid was collected and washed with excess water. This solid was than dried under vacuum at 50° C. for 18h. This solid was taken up in ethyl acetate. The ethyl acetate was washed with 5% HCl, water, brine, and dried over sodium sulfate, filtered and concentrated under vacuum giving the title compound (5.8 g, 92%).
Workup
- customThe ice bath was removed
- temperatureto warm to room temperature over 18 h
- additionThe reaction was poured into water
- customa precipitate formed
- customThe solid was collected
- washwashed with excess water
- customthan dried under vacuum at 50° C. for 18h
- washThe ethyl acetate was washed with 5% HCl, water, brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-1c6d9bf61703426d82438f4e1bed0251
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07910595B2
Reaction notes
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