Water → 4-(Aminomethyl)benzamide
Reaction equation
[NH2:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[OH2:11]>[Cu]>[NH2:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([C:2]([NH2:1])=[O:11])=[CH:4][CH:5]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
In a 100 ml autoclave (manufactured by Nitto Koatsu Co., Ltd., material: SUS-316), 43 g of water, 11.5 g of a water-containing p-aminomethylbenzonitrile (10 g as p-aminomethylbenzonitrile, purity: 86.7%.) and 2.0 g of sponge copper (R-300C, manufactured by NIKKO RICA CORPORATION) were charged and, after sealing the autoclave, the atmosphere in the autoclave was replaced by nitrogen and the reaction was conducted at 100° C. for 6 hours. After the completion of the reaction, the catalyst was collected by filtration and the filtrate was cooled to 5° C., and then the crystal was collected by filtration. 10.0 g of the resulting crystal (wet form, containing 8.05 g of p-aminomethylbenzamide) was suspended in 43 g of water and dissolved with heating to 70° C., followed by cooled again to 5° C., filtration and further drying to obtain 7.99 g of p-aminomethylbenzamide (yield based on p-aminomethylbenzonitrile: 71%). The purity of p-aminomethylbenzamide determined by analyzing using high-performance liquid chromatograph was 99% or higher.
Workup
- additionwere charged
- customAfter the completion of the reaction
- filtrationthe catalyst was collected by filtration
- filtrationthe crystal was collected by filtration
- dissolutiondissolved
- temperaturewith heating to 70° C.
- temperatureby cooled again to 5° C.
- filtrationfiltration
- customfurther drying
Sources & evidence
- ORD record
- ord-29bd6143177d47da8a8a7fcab909b9c6
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07227036B2
Reaction notes
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