Hydrochloric Acid → 3-[2-(tert-Butoxycarbonyl)hydrazinyl]benzoic acid
Reaction equation
[C:1]([O:5][C:6]([NH:8][NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([O:18]C)=[O:17])[CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].Cl>O1CCOCC1>[C:1]([O:5][C:6]([NH:8][NH:9][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=1)[C:16]([OH:18])=[O:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The 4.68 g of unpurified 1-tert-butoxycarbonyl-2-(3-methoxycarbonylphenyl)hydrazine was dissolved in 75 ml of 1,4-dioxane, and 25 ml of aqueous 3N potassium hydroxide solution was added to the solution, followed by heating the mixture at reflux for one hour. The reaction mixture was cooled to 0° C., and about 25 ml of 3N hydrochloric acid was added to make the reaction mixture acidic. The mixture was subjected to salting out and the resultant was extracted with ethyl acetate (2×50 ml). The organic layers were combined, dried and concentrated to obtain 4.40 g of unpurified captioned compound.
Workup
- temperatureby heating the mixture
- temperatureat reflux for one hour
- extractionthe resultant was extracted with ethyl acetate (2×50 ml)
- customdried
- concentrationconcentrated
- customto obtain 4.40 g
Sources & evidence
- ORD record
- ord-25e3398407e44f7c8a2b3c67ad1399c2
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06087369
Reaction notes
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