Hydrochloric Acid → HCID 44203162, compound

HRID 1880437Notes

Reaction equation

HRID 1880437 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:13]([O-])=O)[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].O1CCOCC1.[ClH:22]>CCO.[Pd]>[ClH:22].[NH2:13][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([OH:1])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 5747973Benzoic acid, 3,4-dihydroxy-5-nitro-, methyl ester

Product 1

HCID 44203162HCID 44203162, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of methyl 3,4-dihydroxy-5-nitrobenzoate (11.9 g, 55.8 mmol) in EtOH (200 mL), 4M HCl in dioxane (13.96 mL, 55.8 mmol) and 10% palladium on carbon (4.0 g, 3.76 mmol) were added. The reaction mixture was hydrogenated at atmospheric pressure of H2 for 3 hours (TLC-monitoring). The resulting mixture was filtered and concentrated with the use of a rotary evaporator. The residue was triturated with ether (100 mL). The precipitate was filtered off and vacuum-dried to afford methyl 3-amino-4,5-dihydroxybenzoate hydrochloride (12.0 g, 54.6 mmol, 98% yield).

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationconcentrated with the use of a rotary evaporator
  3. customThe residue was triturated with ether (100 mL)
  4. filtrationThe precipitate was filtered off
  5. customvacuum-dried

Sources & evidence

ORD record
ord-b13ad684960f4791a1cc89945ff7ce42
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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