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

HRID 1176811Notes

Reaction equation

HRID 1176811 reaction equation
[C:1]([C:3](=[C:9](OC(=O)C(C)(C)C)[CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[NH3:22]>C(#N)C>[NH2:22]/[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 72326552HCID 72326552, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
10 °C

Procedure

118.2 g (0.4 mol) of ethyl 2-cyano-3-[(pivaloyl)oxy]-4-ethyl-2-hexenoate were dissolved in acetonitrile and cooled to 10° C. At 10-15° C., 112 g (0.8 mol) of 25% strength ammonia solution were then added dropwise, and the mixture was stirred at 15° C. for 3 h. The organic phases is [sic] washed, dried and concentrated. Recrystallization with diisopropyl ether gave 57.5 g (68% of theory) of the title compound (m.p. 87° C.).

Workup

  1. washwashed
  2. customdried
  3. concentrationconcentrated
  4. customRecrystallization with diisopropyl ether

Sources & evidence

ORD record
ord-7f55e1a36a924a09a2ac084ef69677af
Source dataset
uspto-grants-2010_11
Patent number
US07842832B2

Reaction notes

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