Hydrochloric Acid → HCID 18180255, compound

HRID 2263522Notes

Reaction equation

HRID 2263522 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([N+:11]([O-])=O)=[CH:5][C:4]=1[OH:14].Cl>CO.[Pd]>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([NH2:11])=[CH:5][C:4]=1[OH:14]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 223268672,3-Dimethoxy-5-nitrophenol

Product 1

HCID 18180255HCID 18180255, compoundYield 107%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of 1.1 g of 2,3-dimethoxy-5-nitrophenol in 45 mL dry methanol with 200 mg of 10% Pd/C (Degussa) was hydrogenated under a hydrogen balloon overnight. The reaction was filtered through a bed of celite and evaporated and the residue was chromatographed over silica gel (ethyl acetate/hexanes 3:2 gradient to 100% ethyl acetate). The appropriate fractions were evaporated to dryness to yield an oil that was taken up in methanol to which methanolic HCl solution was added and the solvent evaporated to yield 1.0 g of the desired product 4,5-dimethoxy-3-hydroxyaniline hydrochloride. MS (m/e): 170 (MH+).

Workup

  1. customballoon overnight
  2. filtrationThe reaction was filtered through a bed of celite
  3. customevaporated
  4. customthe residue was chromatographed over silica gel (ethyl acetate/hexanes 3:2 gradient to 100% ethyl acetate)
  5. customThe appropriate fractions were evaporated to dryness
  6. customto yield an oil that
  7. additionwas added
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-1c8c47f5623f4f7ba9b39d2a38506b06
Source dataset
uspto-grants-2010_12
Patent number
US07851480B2

Reaction notes

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