Potassium Cyanide → HCID 85905850, compound
Reaction equation
[CH3:1][C:2]([CH3:9])([CH:7]=O)[C:3]([O:5][CH3:6])=[O:4].S(=O)(O)[O-].[Na+].[OH-].[NH4+:16].[C-:17]#[N:18].[K+]>O>[NH2:16][CH:7]([C:17]#[N:18])[C:2]([CH3:1])([CH3:9])[C:3]([O:5][CH3:6])=[O:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
A solution of methyl 2,2-dimethyl-3-oxopropanoate (29-1, 6.50 g, 49.9 mmol, 1 equiv), sodium bisulfite (10.4 g, 99.9 mmol, 2.00 equiv), and concentrated ammonium hydroxide (15 M, 33.3 mL, 499 mmol, 10.0 equiv) in water (200 mL) was stirred at 23° C. for 20 minutes, then potassium cyanide (6.51 g, 99.9 mmol, 2.00 equiv) was added. The resulting mixture was stirred at 23° C. for 20 hours, then extracted with ethyl ether (3×100 mL). The combined organic layers were washed with brine, then dried over sodium sulfate and concentrated to provide methyl 3-amino-3-cyano-2,2-dimethylpropanoate (29-2) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 3.93 (br m, 1H), 3.93 (s, 3H), 1.76 (br s, 2H), 1.36 (s, 3H), 1.35 (s, 3H).
Workup
- extractionextracted with ethyl ether (3×100 mL)
- washThe combined organic layers were washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-daa11c1be66443ec82b91fc944040b7a
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07348440B2
Reaction notes
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