Acetone → HCID 86722321, compound
Reaction equation
[C:1]([O:6][C:7]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])(=[O:5])[CH2:2][CH2:3][CH3:4].[ClH:19].[H][H].CC(C)=O>O1CCOCC1.[Pd]>[ClH:19].[C:1]([O:6][C:7]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])(=[O:5])[CH2:2][CH2:3][CH3:4]Participants
Conditions
- Temperature
- 25 °C
Procedure
10 g of 2-butanoyloxy-5-nitro-benzoic acid, 8.5 ml of dioxane, 1.5 ml of HCl 4M solution in dioxane and 1.0 g of Pd/C at 5% were loaded into a 300 ml reactor at 16±2° C. After two vacuum-nitrogen cycles, the reactor was saturated with hydrogen at 10 bar and kept at 16±2° C. for 6 hours. At the end, nitrogen atmosphere was restored in the reactor and the reaction mixture was added with 125 ml of acetone at 25° C. The suspension was stirred at 25° C. for 30 minutes to obtain the dissolution of the undissolved product and the carbon suspension was filtered on a celite panel which was then washed with 60 ml of acetone. The resultant solution was then evaporated under vacuum at 30° C. and the solid residue was dried under vacuum at 35° C. for 4 hours to obtain 10 g of the expected product (99% yield).
Workup
- customto obtain
- dissolutionthe dissolution of the undissolved product
- filtrationthe carbon suspension was filtered on a celite panel which
- washwas then washed with 60 ml of acetone
- customThe resultant solution was then evaporated under vacuum at 30° C.
- customthe solid residue was dried under vacuum at 35° C. for 4 hours
Sources & evidence
- ORD record
- ord-3f81788c2a514014a98fb86c266bedcb
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096491B2
Reaction notes
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