2-Amino-3,5-dibromobenzaldehyde → HCID 178479018, compound
Reaction equation
[ClH:1].[Br:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([NH2:9])[CH2:5][CH2:4]1.[NH2:10][C:11]1[C:18]([Br:19])=[CH:17][C:16]([Br:20])=[CH:15][C:12]=1[CH:13]=O.[H][H]>[Ni]>[ClH:1].[NH2:10][C:11]1[C:18]([Br:19])=[CH:17][C:16]([Br:20])=[CH:15][C:12]=1[CH2:13][NH:9][C@H:6]1[CH2:7][CH2:8][C@H:3]([Br:2])[CH2:4][CH2:5]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 35 °C
Procedure
179 g of trans-1-bromo-4-aminocyclohexane hydrochloride and 279 g of 2-amino-3,5-dibromobenzaldehyde are put into a suitable flask. The temperature rises to 60° C. and the mixture is then cooled to 35° C., after which 250 ml of ethylic alcohol are added. The solution is transferred to a suitable, steel reactor for high-pressure hydrogenizing. 10 g of Nickel-Raney are added, the reactor vessel is closed and hydrogen gas is introduced at 1000 psi. The vessel is agitated at ambient temperature for 15 minutes. The contents of the vessel are poured out and the catalyst is filtered. The ether is evaporated under vacuum. The residue is dissolved in 300 ml of absolute ethylic alcohol followed by the addition of gaseous HCl. THe desired product crystallizes and is recrystallized using absolute ethylic alcohol. 300 g of product are obtained which has a melting point of 240°-245° C.
Workup
- customrises to 60° C.
- customthe reactor vessel is closed
- additionThe contents of the vessel are poured out
- filtrationthe catalyst is filtered
- customThe ether is evaporated under vacuum
- dissolutionThe residue is dissolved in 300 ml of absolute ethylic alcohol
- additionfollowed by the addition of gaseous HCl
- customTHe desired product crystallizes
- customis recrystallized
Sources & evidence
- ORD record
- ord-bd0b5aefd1fd4e04a33a3929a298629b
- Source dataset
- uspto-grants-1985_07
- Patent number
- US04528393
Reaction notes
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