Aniline → HCID 57897948, compound

HRID 1693533Notes

Reaction equation

HRID 1693533 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH:5]([NH2:8])[C:6]#[N:7])[CH3:2].[C:10](OCC)(OCC)(OCC)[CH2:11][CH3:12].[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(#N)C>[CH2:1]([O:3][C:4]([C:5]1[N:8]=[C:10]([CH2:11][CH3:12])[N:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:6]=1[NH2:7])=[O:9])[CH3:2]

Participants

5

Reactant 3

HCID 6115AnilineHCID 66995Ethyl orthopropionateHCID 288716Ethyl 2-amino-2-cyanoacetate

Product 1

HCID 57897948HCID 57897948, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of amino-cyano-acetic acid ethyl ester (400 mg, 3.12 mmol) and triethyl orthopropionate (629 μL, 3.12 mmol) in acetonitrile is heated at reflux for 45 minutes. After cooled down to room temperature, aniline (285 μL, 3.12 mmol) is added. After stirred at room temperature overnight, the solution is concentrated and purified with flash chromatography. A pale yellow solid is obtained as the desired product: 1H NMR (CDCl3) δ 7.56 (m, 3H), 7.29 (m, 2H), 4.77 (b, 2H), 4.37 (q, 2H), 2.49 (q, 2H), 1.40 (t, 3H), 1.11 (t, 3H); m/z 260.1 (M+1).

Workup

  1. temperatureat reflux for 45 minutes
  2. concentrationthe solution is concentrated
  3. custompurified with flash chromatography

Sources & evidence

ORD record
ord-d24d594f435c48b994e2111f2802af1c
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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