3-Nitroaniline → HCID 57899406, compound

HRID 1024613Notes

Reaction equation

HRID 1024613 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.[N+:20]([C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26])([O-:22])=[O:21]>C(#N)C>[CH2:1]([O:3][C:4]([C:5]1[N:8]=[CH:10][N:26]([C:25]2[CH:27]=[CH:28][CH:29]=[C:23]([N+:20]([O-:22])=[O:21])[CH:24]=2)[C:6]=1[NH2:7])=[O:9])[CH3:2]

Participants

5

Reactant 3

HCID 74233-NitroanilineHCID 31214Ethyl orthoformateHCID 288716Ethyl 2-amino-2-cyanoacetate

Product 1

HCID 57899406HCID 57899406, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of amino-cyano-acetic acid ethyl ester (17.06 g, 133.3 mmol) and triethyl orthoformate (19.7 g, 133.3 mmol) in acetonitrile (175 mL) is heated at reflux for 45 min. The reaction mixture is allowed to reach rt and 3-nitro aniline (18.4 g, 133.3 mmol) is added and stirred at rt for 12 h. The crude product obtained is purified by column chromatography to afford the product as pale yellow solid (1).

Workup

  1. temperatureat reflux for 45 min
  2. customto reach rt
  3. customThe crude product obtained
  4. customis purified by column chromatography

Sources & evidence

ORD record
ord-e51ab6d22d85413ab42403e990df55c9
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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