Diethyl 3-nitrobenzene-1,2-dicarboxylate → Diethyl 3-aminobenzene-1,2-dicarboxylate
Reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]1[C:6](=[C:12]([N+:16]([O-])=O)[CH:13]=[CH:14][CH:15]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2]>O1CCOCC1.[Ni]>[CH2:1]([O:3][C:4](=[O:19])[C:5]1[C:6](=[C:12]([NH2:16])[CH:13]=[CH:14][CH:15]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
69.7 g (0.26 mol) of 3-nitrophthalic acid diethyl ester in 690 ml of dioxane are hydrogenated in the presence of 7 g of a Raney nickel catalyst to give 3-aminophthalic acid diethyl ester. The reaction solution is filtered and 30.4 g (0.31 mol) of maleic anhydride are added, at room temperature, to the filtrate. The reaction mixture is kept at 25° C. for 12 hours and then concentrated in vacuo. 75 ml of acetic anhydride and 12.7 g of sodium acetate are added to the residue and the mixture is heated to 80° C. for 45 minutes and diluted with 500 ml of water. The crystalline precipitate is rinsed with water and dried in vacuo at 45° C. 68 g (82% of theory) of crystalline 3-maleimidyl-phthalic acid diethyl ester are obtained; melting point 86°-90° C. When the product is recrystallised from ethanol, the melting point rises to 92°-93° C.
Sources & evidence
- ORD record
- ord-73d7a35f8b3d4714ba5e087fb2a9852a
- Source dataset
- uspto-grants-1979_01
- Patent number
- US04134895
Reaction notes
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