Ammonia → 2-Cyanoethyl 3-amino-2-butenoate

HRID 1110346Notes

Reaction equation

HRID 1110346 reaction equation
[C:1]([O:7][CH2:8][CH2:9][C:10]#[N:11])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[NH3:12]>CO>[NH2:12][C:3]([CH3:5])=[CH:2][C:1]([O:7][CH2:8][CH2:9][C:10]#[N:11])=[O:6]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 123604062-Cyanoethyl 3-oxobutanoate

Product 1

HCID 731858132-Cyanoethyl 3-amino-2-butenoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 10 mL of methanol was added 20 g (0.13 mole) of 2-cyanoethyl acetoacetate. The solution was cooled in ice and a slow stream of ammonia gas was passed through it for five hours. The reaction flask was stoppered and stored at 0° C. overnight. The resulting solid was collected, washed with a small amount of methanol and dried under high vacuum to give 11.1 g (0.072 mole) of 2-cyanoethyl 3-aminobut-2-enoate, 1H NMR 4.6 (s, 1H), 4.3 (t, 2H), 2.8 (t, 2H), 2.0(t, 3H).

Workup

  1. temperatureThe solution was cooled in ice
  2. customThe resulting solid was collected
  3. washwashed with a small amount of methanol
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-659da49c72a340e59d6911e1e26c0d8c
Source dataset
uspto-grants-1990_12
Patent number
US04975437

Reaction notes

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