Hydrochloric Acid → HCID 18180255, compound

HRID 226208Notes

Reaction equation

HRID 226208 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 ballon 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. filtrationThe reaction was filtered through a bed of celite
  2. customevaporated
  3. customthe residue was chromatographed over silica gel (ethyl acetate/hexanes 3:2 gradient to 100% ethyl acetate)
  4. customThe appropriate fractions were evaporated to dryness
  5. customto yield an oil that
  6. additionwas added
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-a1c20588562948399ed3bb6d4a734f4d
Source dataset
uspto-grants-2009_07
Patent number
US07557207B2

Reaction notes

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