3-Chloroaniline → Acetic acid, chloro[(3-chlorophenyl)hydrazono]-, ethyl ester
Reaction equation
O.O.O.C([O-])(=O)C.[Na+].[Cl:9][CH:10](C(C)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12].N([O-])=O.[Na+].[Cl:23][C:24]1[CH:25]=[C:26]([NH2:30])[CH:27]=[CH:28][CH:29]=1.[Cl-].C1([N+:38]#N)C=CC=CC=1>C(O)C.O.Cl>[Cl:9][C:10](=[N:38][NH:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([Cl:23])[CH:25]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12]Participants
9
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
12.2 g (149 mmol) sodium acetate trihydrate was added to a solution of 15.5 g (94.1 mmol) ethyl 2-chloroacetoacetate in 300 mL ethanol. The solution was cooled to 0° C. A parallel reaction consisted of the addition of an ice-cold aqueous solution of 6.49 g (94.1 mmol) sodium nitrite in 30 mL water to a solution of 10.0 g (78.4 mol) 3-chloro-phenylamine in 75 mL 6N aqueous HCl. The cold solution of phenyldiazonium chloride was then added to the ester mixture at 0° C. and stirred for 3 h at 0° C. The resulting mixture was diluted with water and ice and stirred for 2 h at 0° C. The precipitate was filtered off, washed with water, dried and used without further purification for the next synthesis step (yield: 13.0 g (64%)).
Workup
- customA parallel reaction
- stirringstirred for 2 h at 0° C
- filtrationThe precipitate was filtered off
- washwashed with water
- customdried
- customused without further purification for the next synthesis step (yield: 13.0 g (64%))
Sources & evidence
- ORD record
- ord-e459ed67dbe34bba85956712a8587ecb
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08883789B2
Reaction notes
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