Ethyl Acetate → 2-Amino-4-bromopyridine-3-carbonitrile
Reaction equation
Br[C:2]1[N:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:3]=1[C:4]#[N:5].CCOC(C)=O.[NH4+:17].[OH-]>C1COCC1>[NH2:17][C:2]1[N:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:3]=1[C:4]#[N:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of compound D7 (32 g, 122.2 mmol) in NH4OH (200 ml, 30% in water) and THF (200 ml) was heated at 100° C. for 12 h. in a PARR pressure vessel. After cooling, EtOAc was added. The organic layer was separated, washed with brine, dried (Na2SO4) and evaporated in vacuo. The solid residue thus obtained was triturated with DCM and then filtered off. The filtrate was evaporated in vacuo to yield compound D8 (6.5 g, 26.8%) as a white solid.
Workup
- temperatureAfter cooling
- customThe organic layer was separated
- washwashed with brine
- dry with materialdried (Na2SO4)
- customevaporated in vacuo
- customThe solid residue thus obtained
- customwas triturated with DCM
- filtrationfiltered off
- customThe filtrate was evaporated in vacuo
Sources & evidence
- ORD record
- ord-b0c1fb4648cf453d845e32f0ef0125d0
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691813B2
Reaction notes
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