Formic Acid → 2-(beta-Methoxyethyl)amino-6-(beta-methoxyethyl)aminonitrobenzene
Reaction equation
C.Cl[C:3]1[CH:8]=[C:7]([NH:9][CH2:10][CH2:11][O:12][CH3:13])[C:6]([N+:14]([O-:16])=[O:15])=[C:5]([NH:17][CH2:18][CH2:19][O:20][CH3:21])[CH:4]=1.C(O)=O>C(N(CC)CC)C.O.[Pd]>[CH3:21][O:20][CH2:19][CH2:18][NH:17][C:5]1[CH:4]=[CH:3][CH:8]=[C:7]([NH:9][CH2:10][CH2:11][O:12][CH3:13])[C:6]=1[N+:14]([O-:16])=[O:15]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
0.4 g of palladium at a concentration of 10% on active charcoal is added to 0.084 mole (25.5 g) of 4-chloro-2-(β-methoxyethyl)amino-6-(β-methoxyethyl)aminonitrobenzene in 33.4 ml of triethylamine, after which 7 ml of formic acid are added dropwise. At the end of the additions, the reaction mixture is heated for 1 hour 30 minutes, under reflux. The reaction mixture is diluted with 100 ml of 96° alcohol and 100 ml of water. The expected product precipitates. After filtration, the expected product containing the catalyst is dissolved in 90 ml of isopropyl alcohol. The catalyst is removed by hot filtration. The expected product crystallizes.
Workup
- temperatureAt the end of the additions, the reaction mixture is heated for 1 hour 30 minutes
- temperatureunder reflux
- customThe expected product precipitates
- filtrationAfter filtration
- additionthe expected product containing the catalyst
- dissolutionis dissolved in 90 ml of isopropyl alcohol
- customThe catalyst is removed by hot filtration
- customThe expected product crystallizes
Sources & evidence
- ORD record
- ord-abb8d79a029b42918187e3d6971550f6
- Source dataset
- uspto-grants-1991_02
- Patent number
- US04992586
Reaction notes
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