3,5-Dinitrobenzyl alcohol → (3-Amino-5-nitrophenyl)methanol

HRID 2303989Notes

Reaction equation

HRID 2303989 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-])=O)[CH:11]=1)[CH2:7][OH:8])([O-:3])=[O:2].[NH4+]=S>CO>[NH2:12][C:10]1[CH:9]=[C:6]([CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:11]=1)[CH2:7][OH:8]

Participants

3

Reactant 1

HCID 1169783,5-Dinitrobenzyl alcohol

Product 1

HCID 15540036(3-Amino-5-nitrophenyl)methanolYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3,5-dinitrobenzyl alcohol (129.1 g, 0.65 mol; from step (i) above) in MeOH (1500 mL) at reflux was added ammonium sulfide (450 mL, 442.9 g of 20 wt % in H2O, 1.30 mol) over 45 min. The resulting heterogeneous mixture was refluxed for 2 h and stirred at 25° C. for 18 h. The solution was filtered through a pad of Celite, the filtrate was acidified with 2N HCl and the MeOH distilled off in vacuo. The remaining acidic aqueous solution was washed with Et2O (3×) and basified with 6N NaOH. The basic aqueous solution was extracted with Et2O (4×). The organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford 95.8 g (88%) of the sub-title compound as an orange solid which was used without further purification.

Workup

  1. temperatureThe resulting heterogeneous mixture was refluxed for 2 h
  2. filtrationThe solution was filtered through a pad of Celite
  3. distillationthe MeOH distilled off in vacuo
  4. washThe remaining acidic aqueous solution was washed with Et2O (3×)
  5. extractionThe basic aqueous solution was extracted with Et2O (4×)
  6. dry with materialThe organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05bce016db55421684261f28b71a873b
Source dataset
uspto-grants-2002_08
Patent number
US06433186B1

Reaction notes

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