Ammonia → Ethylbenzoate,3-(aminomethyl)
Reaction equation
[C:1]([C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH2:9]Br)([O:3][CH2:4][CH3:5])=[O:2].[NH3:14]>C(#N)C>[C:1]([C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH2:9][NH2:14])([O:3][CH2:4][CH3:5])=[O:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
3-Carboethoxybenzyl bromide (1 ml; Heterocycles, 1977, 6, 5) was added to a saturated solution of ammonia in acetonitrile (30 ml) which had been cooled to -30° C. The mixture was stirred and allowed to warm to laboratory temperature. The mixture was filtered and the filtrate was evaporated. The residue was purified by chromatography on a silica gel column using a 10:1 v/v mixture of ethyl acetate and methanol as eluent. There was thus obtained as an oil 3-carboethoxybenzylamine (0.4 g) which was used without further purification as the appropriate amine in the process described in Example 1.
Workup
- temperatureto warm to laboratory temperature
- filtrationThe mixture was filtered
- customthe filtrate was evaporated
- customThe residue was purified by chromatography on a silica gel column
- additiona 10:1 v/v mixture of ethyl acetate and methanol as eluent
Sources & evidence
- ORD record
- ord-9f6df400563440bf9d658ee6735f15f9
- Source dataset
- uspto-grants-1993_10
- Patent number
- US05252573
Reaction notes
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