HCID 59079947, compound → HCID 59134962, compound

HRID 1994113Notes

Reaction equation

HRID 1994113 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:6]=1[Cl:14])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O>[C:1]([C:5]1[CH:10]=[C:9]([CH:8]=[CH:7][C:6]=1[Cl:14])[NH2:11])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 59079947HCID 59079947, compound

Product 1

HCID 59134962HCID 59134962, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-tert-butyl-1-chloro-4-nitrobenzene (505 mg, 2.36 mmol) in EtOAc (25 mL) was added SnCl2 hydrate (906 mg, 3.55 mmol). This mixture was heated at reflux and the solids dissolved. After 2 h, additional SnCl2 hydrate (906 mg, 3.55 mmol) was added and the solution was heated at reflux for another 2 h. The reaction mixture was purified by column chromatography (SiO2, 20% EtOAc/Hex) to give 210 mg of the title compound as a yellow oil (48%). 1H NMR (400 MHz, CD3OD) δ: 6.68 (d, 1H), 6.16 (d, 1H), 6.02 (dd, 1H), and 0.92 (s, 9H).

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux
  3. dissolutionthe solids dissolved
  4. temperaturethe solution was heated
  5. temperatureat reflux for another 2 h
  6. customThe reaction mixture was purified by column chromatography (SiO2, 20% EtOAc/Hex)

Sources & evidence

ORD record
ord-7129dd61ddba451b92b6db2b3df8cdb9
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

Loading…