Ammonia → Ethyl (2Z)-3-amino-2-cyano-4-ethyl-2-hexenoate

HRID 1176810Notes

Reaction equation

HRID 1176810 reaction equation
[C:1]([C:3](=[C:9](OC)[CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[NH3:17]>C1COCC1>[NH2:17]/[C:9](/[CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])=[C:3](/[C:1]#[N:2])\[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 72326554Ethyl 2-cyano-3-methoxy-4-ethyl-2-hexenoate

Product 1

HCID 11564730Ethyl (2Z)-3-amino-2-cyano-4-ethyl-2-hexenoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

At 10° C., 52 g (0.23 mol) of ethyl 2-cyano-3-methoxy-4-ethyl-2-hexenoate were initially charged in THF, and 20 g (0.3 mol) of 25% strength ammonia solution were added. After 2 h of stirring at 25° C., the solution was concentrated, the residue was taken up in n-hexane/diisopropyl ether (1:1) and the precipitate was filtered off with suction.

Workup

  1. concentrationthe solution was concentrated
  2. filtrationthe precipitate was filtered off with suction

Sources & evidence

ORD record
ord-184c1f0b375c439da72cf900d2fb7f73
Source dataset
uspto-grants-2010_11
Patent number
US07842832B2

Reaction notes

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