Hydrochloric Acid → HCID 71254993, compound
Reaction equation
[Cl:1][C:2]1[C:3]([F:15])=[C:4]([NH:8]/[N:9]=[C:10](/Cl)\[C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.Cl[C:17]1C(F)=C(C=C[CH:23]=1)N.Cl.N([O-])=O.[Na+].[C:30]([O-:33])(=[O:32])[CH3:31].[Na+].ClC(C(=O)C)C(=O)C>O.CO>[C:11]([C:10]1[C:31]([C:30]([OH:33])=[O:32])=[C:17]([CH3:23])[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=2[F:15])[N:9]=1)(=[O:13])[CH3:12]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
(E)-N′-(3-Chloro-2-fluorophenyl)-2-oxopropanehydrazonoyl chloride: To a solution of 3-chloro-2-fluoroaniline (1.511 mL, 13.74 mmol) in HCl (116 mL, 116 mmol) at 0° C. was added a solution of sodium nitrite (1.896 g, 27.5 mmol) in water (12 mL) dropwise while maintaining the temperature at 0° C. After completion of addition, the reaction was stirred at the same temperature for additional 30 mins. The pH of the reaction mixture was adjusted to 4.5 using solid sodium acetate. The resultant mixture was then treated dropwise with 3-chloropentane-2,4-dione (2.129 mL, 17.86 mmol) in methanol (12 mL). After completion of addition, the reaction mixture was allowed to warm to room temperature and stirred at room temperature overnight. The reaction mixture was diluted with water and then extracted with ether. The crude product was then purified by silica gel chromatography to isolate the desired product. MS(ESI) m/z: 249.0 (M+2H)+.
Workup
- additionAfter completion of addition
- additionAfter completion of addition
- temperatureto warm to room temperature
- stirringstirred at room temperature overnight
- extractionextracted with ether
- customThe crude product was then purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-ff8e9a16ad8246d9b73139dc5abd771e
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221818B2
Reaction notes
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