Ethanol → Ethyl acetate methanol ammonia

HRID 1868353Notes

Reaction equation

HRID 1868353 reaction equation
Cl[C:2]1[CH:7]=CC(Cl)=CC=1[N+:9]([O-])=O.Cl[Sn]Cl.[C:15]([O-])(O)=[O:16].[Na+].[CH3:20][CH2:21][OH:22]>>[NH3:9].[CH3:15][OH:16].[CH3:20][CH2:21][O:22][C:2]([CH3:7])=[O:16]

Participants

5

Reactant 4

HCID 702EthanolHCID 69772,5-DichloronitrobenzeneHCID 24479Stannous ChlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 21873639Ethyl acetate methanol ammoniaYield 5%

Conditions

Temperature
20 °C

Procedure

Compound 15 was prepared using the procedures of Steps 1-2 of Example 5, substituting 5-bromo-2-fluoronitrobenzene for 2,5-dichloronitrobenzene in Step 1. Step 3: A suspension of 15 (6.2 g, 10 mmol) in EtOH (20 ml) was treated with SnCl2 (9.5 g, 50 mmol), heated to reflux for 3 h, and then stirred overnight at 20° C. The reaction mixture was poured on saturated aqueous NaHCO3, extracted with CH2Cl2, dried over Na2SO4, and concentrated. Chromatography (5% 1 N NH3-MeOH/EtOAc) provided the title compound (5.2 g, 52%) as a yellow solid. MS: (M+1) 487.

Workup

  1. customCompound 15 was prepared
  2. temperatureheated
  3. temperatureto reflux for 3 h
  4. extractionextracted with CH2Cl2
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fc1a52b3d5094d27908370497939dc4c
Source dataset
uspto-grants-2009_12
Patent number
US07635705B2

Reaction notes

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