Ammonia → HCID 86759162, compound

HRID 1167148Notes

Reaction equation

HRID 1167148 reaction equation
[C:1]([CH2:3][CH2:4][C:5](=O)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])#[N:2].[NH3:13]>>[NH2:13][C:5]([CH2:4][CH2:3][C:1]#[N:2])=[CH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 22995884HCID 22995884, compound

Product 1

HCID 86759162HCID 86759162, compoundYield 95%

Procedure

3.80 g (22.4 mmol) of ethyl 5-cyano-3-oxopentanoate were taken up in 5 ml of a saturated ethanolic ammonia solution and stirred at room temperature for 24 h. The volatile components were distilled off using a rotary evaporator, giving 3.60 g (95%) of ethyl 3-amino-5-cyano-2-pentenoate. 1H-NMR (300 MHz, DMSO) 1.16 (t, 3H), 2.37 (t, 2H), 2.75 (t, 2H), 3.99 (q, 2H), 4.41 (s, 1H), 6.96 (s, broad, 1H), 7.69 (s, broad, 1H). MS (DCI/NH3): 169 (M+H)+, 186 (M+NH4)+, 337 (2M+H)+.

Workup

  1. distillationThe volatile components were distilled off
  2. customa rotary evaporator

Sources & evidence

ORD record
ord-c893d7728ea24589a4704c880b0aca6e
Source dataset
uspto-grants-2003_09
Patent number
US06617332B1

Reaction notes

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