Triethylamine → HCID 57736565, compound

HRID 536336Notes

Reaction equation

HRID 536336 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:7]([N+:11]([O-])=O)=[CH:6][C:3]=1[C:4]#[N:5].[Sn](Cl)(Cl)(Cl)Cl.C(N(CC)CC)C>C(O)C>[NH2:11][C:7]1[C:8]([CH3:10])=[CH:9][C:2]([Br:1])=[C:3]([CH:6]=1)[C:4]#[N:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24287Tin tetrachlorideHCID 57736551HCID 57736551, compound

Product 1

HCID 57736565HCID 57736565, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-bromo-4-methyl-5-nitrobenzonitrile (500 mg, 2.07 mmol) in ethanol (20 mL) was added tin chloride (785 mg, 4.14 mmol). The mixture was refluxed for 5 h. After cooling to room temperature, triethylamine (1.01 g, 10 mmol) was added. The mixture was concentrated and purified by silica chromatography (30-50% ethyl acetate in hexanes gradient) to afford 5-Amino-2-bromo-4-methylbenzonitrile a as beige solid; ESMS m/z 211 (M+H+).

Workup

  1. temperatureThe mixture was refluxed for 5 h
  2. concentrationThe mixture was concentrated
  3. custompurified by silica chromatography (30-50% ethyl acetate in hexanes gradient)

Sources & evidence

ORD record
ord-08a4db77db524e80bf66e24c45ad1438
Source dataset
uspto-grants-2014_10
Patent number
US08859574B2

Reaction notes

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