Formic Acid → (3-Amino-5-nitrophenyl)methanol

HRID 1107219Notes

Reaction equation

HRID 1107219 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].C(N(CC)CC)C.C(O)=O>C(OCC)(=O)C.[Pd]>[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

6

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 1169783,5-Dinitrobenzyl alcohol

Product 1

HCID 15540036(3-Amino-5-nitrophenyl)methanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A three neck flask fitted with a reflux condenser and an addition funnel was charged with 3,5-dinitrobenzyl alcohol (10 g, 50 mmol), 10% Pd/C (630 mg) and triethylamine (35 mL, 251 mmol). This was placed in a 70° C. oil bath and through the addition funnel was added 90% formic acid (10 mL, 234 mmol) dropwise. The reaction was heated for 30 minutes and cooled to room temperature. The clear yellow supernatant was filtered through celite and the lower layer containing the catalyst was treated with acetone, filtered through celite and rinsed with acetone. The filtered organic layers were combined and concentrated to give an orange oil. The oil was diluted in ethyl acetate which was washed with H2O, dried (MgSO4), filtered and concentrated to give crude 3-amino-5-nitrobenzyl alcohol as an orange solid.

Workup

  1. customA three neck flask fitted with a reflux condenser and an addition funnel
  2. customThis was placed in a 70° C.
  3. temperatureThe reaction was heated for 30 minutes
  4. filtrationThe clear yellow supernatant was filtered through celite
  5. additionthe lower layer containing the catalyst
  6. additionwas treated with acetone
  7. filtrationfiltered through celite
  8. washrinsed with acetone
  9. concentrationconcentrated
  10. customto give an orange oil
  11. washwas washed with H2O
  12. dry with materialdried (MgSO4)
  13. filtrationfiltered
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-86e9daa3a1b3495195d338baeb5c2b81
Source dataset
uspto-grants-2000_05
Patent number
US06060038

Reaction notes

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