Ammonia → 2-Amino-2-(3-ethoxy-4-isopropoxyphenyl)acetonitrile
Reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[CH:7]=O)[CH3:2].C[Si]([C:20]#[N:21])(C)C.[NH3:22]>CO>[NH2:22][CH:7]([C:6]1[CH:9]=[CH:10][C:11]([O:12][CH:13]([CH3:15])[CH3:14])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)[C:20]#[N:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3-Ethoxy-4-isopropoxybenzaldehyde (WO 2004072101) (24 g, 115 mmol) was dissolved in a 7N MeOH solution of ammonia (200 mL) and the whole was cooled to 0° C. Trimethylsilyl cyanide (24 mL, 180 mmol) was added and the reaction mixture was stirred overnight with gradual warming to rt. The reaction product was concentrated to provide 2-amino-2-(3-ethoxy-4-isopropoxyphenyl)acetonitrile (29 g, 100%) as a yellow oil. The oil (23 g) was dissolved in ethyl ether (460 mL), cooled to 0° C., and HCl (g) was bubbled through the solution for 5 min. The resulting precipitate was filtered and dried on the high vac to provide Intermediate 13A (19 g, 72%) as a yellow solid.
Workup
- temperaturewith gradual warming to rt
- concentrationThe reaction product was concentrated
Sources & evidence
- ORD record
- ord-7bf2923947a04d6f856f0cc88b33b4bf
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07456195B2
Reaction notes
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