4-Nitrobenzaldehyde → HCID 73098955, compound
Reaction equation
[CH3:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[N+:16]([C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)([O-:18])=[O:17]>O1CCCC1.O.[Cl-].[Zn+2].[Cl-]>[N+:16]([C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[CH:1][C:2]2[C:15]3[C:10]([N:9]=[C:8]4[C:3]=2[CH:4]=[CH:5][CH:6]=[CH:7]4)=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:21][CH:20]=1)([O-:18])=[O:17]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 130 °C
Procedure
A mixture of 9-methylacridine (4.83 g, 25.0 mmol), 4-nitrobenzaldehyde (4.23 g, 31.25 mmol) and zinc chloride (5.06 g, 31.25 mmol) is heated at 130° C. for 3 hours with an oil bath. The solid recovered is heated in a solution of sodium metabisulfite in order to eliminate the excess aldehyde and the hot mixture is filtered. Precipitates obtained are dissolved in a minimum amount of tetrahydrofuran and water is added to the solution so as to obtain the product in the form of precipitates. These precipitates are recovered by filtration and dried. The product can be recrystallized from ethanol. The yield is 35%.
Workup
- customThe solid recovered
- temperatureis heated in a solution of sodium metabisulfite in order
- filtrationthe hot mixture is filtered
- customPrecipitates
- customobtained
- additionis added to the solution so as
- customto obtain the product in the form
- customof precipitates
- filtrationThese precipitates are recovered by filtration
- customdried
- customThe product can be recrystallized from ethanol
Sources & evidence
- ORD record
- ord-6365a65917e243f8801d5fc57c5ecc48
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07223865B2
Reaction notes
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