3-Aminobenzonitrile → HCID 57899388, compound

HRID 1024633Notes

Reaction equation

HRID 1024633 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH:5]([NH2:8])[C:6]#[N:7])[CH3:2].[CH:10](OCC)(OCC)OCC.[NH2:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[C:24]#[N:25]>C(#N)C>[CH2:1]([O:3][C:4]([C:5]1[N:8]=[CH:10][N:20]([C:21]2[CH:28]=[CH:27][CH:26]=[C:23]([C:24]#[N:25])[CH:22]=2)[C:6]=1[NH2:7])=[O:9])[CH3:2]

Participants

5

Reactant 3

HCID 167023-AminobenzonitrileHCID 31214Ethyl orthoformateHCID 288716Ethyl 2-amino-2-cyanoacetate

Product 1

HCID 57899388HCID 57899388, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of amino-cyano-acetic acid ethyl ester (10.6 g, 83.3 mmol) and triethyl orthoformate (12.35 g, 83.3 mmol) in acetonitrile (110 mL) is heated at reflux for 45 min. The reaction mixture is allowed to reach rt and 3-amino-benzonitrile (9.80 g, 83.3 mmol) is added and stirred at rt for 48 h. The crude product obtained is purified by column chromatography (1).

Workup

  1. temperatureat reflux for 45 min
  2. customto reach rt

Sources & evidence

ORD record
ord-d8c15f7ac5924e7a86924f440d67312a
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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