Hydrochloric Acid → Ethyl 2-(4-cyano-2-methoxyphenyl)-3-(dimethylamino)acrylate
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][C:13]([CH3:16])(C)C)=[O:11])=[C:5]([O:17][CH3:18])[CH:4]=1)#[N:2].Cl.O1CCOCC1.C(C1C=CC(CC(OCC)=O)=C(OC)C=1)#N.C(O[CH:45](OCC)[N:46]([CH3:48])[CH3:47])C>C(O)C.CN(C=O)C.CCOC(C)=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=[CH:45][N:46]([CH3:48])[CH3:47])[C:10]([O:12][CH2:13][CH3:16])=[O:11])=[C:5]([O:17][CH3:18])[CH:4]=1)#[N:2]Participants
9
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
Combined tert-butyl 2-(4-cyano-2-methoxyphenyl)acetate (549 mg, 2.218 mmol) and 4N HCl in dioxane (0.277 mL, 1.109 mmol) in ethanol (7.4 mL) and stirred for 16 hours at 60° C. The reaction was concentrated by rotary evaporation and then combined with ethyl 2-(4-cyano-2-methoxyphenyl)acetate (0.486 g, 2.217 mmol) and 1,1-diethoxy-N,N-dimethylmethanamine (1.9 mL, 11.08 mmol) in DMF (4.43 mL) and stirred for 16 hours at 100° C. The reaction mixture was diluted with 200 mL EtOAc and washed twice with 200 mL water. Organic layer was dried with sodium sulfate and concentrated to give a residue which was purified on a 60 g NH silica gel column eluting with hexanes and EtOAc to give the title compound (405 mg, 74%).
Workup
- concentrationThe reaction was concentrated by rotary evaporation
- washwashed twice with 200 mL water
- dry with materialOrganic layer was dried with sodium sulfate
- concentrationconcentrated
- customto give a residue which
- customwas purified on a 60 g NH silica gel column
- washeluting with hexanes and EtOAc
Sources & evidence
- ORD record
- ord-8e16190dd5b04168948c0b4c0bd1e4ca
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09345713B2
Reaction notes
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