Hydrochloric Acid → 3-Acetoxy-5-amino-4-methoxy-benzoic acid

HRID 521458Notes

Reaction equation

HRID 521458 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([N+:16]([O-])=O)[C:13]=1[O:14][CH3:15])[C:8]([OH:10])=[O:9])(=[O:3])[CH3:2].Cl.[H][H]>C(O)C.CO.[Pd]>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([NH2:16])[C:13]=1[O:14][CH3:15])[C:8]([OH:10])=[O:9])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 129240253-Acetoxy-4-methoxy-5-nitro-benzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 129240263-Acetoxy-5-amino-4-methoxy-benzoic acidYield 103.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

3-Acetoxy-4-methoxy-5-nitro-benzoic acid (4.50 g, 17.6 mmol) (R. T. Borchardt et al., J. Med. Chem. 25 (1982), 312-323; F. Tiemann et al., Ber. dt. Chem. Ges. 9 (1876), 937) was dissolved in ethanol (180 ml) and 0.5 M hydrogen chloride in methanol (4 ml) and hydrogenated in an H-Cube™ hydrogenation reactor with 100 bar hydrogen at 40° C. over a 10% palladium on charcoal cartridge. The mixture was evaporated to dryness to give 4.1 g of the title compound.

Workup

  1. customat 40° C.
  2. customThe mixture was evaporated to dryness

Sources & evidence

ORD record
ord-4e9ccf626fd14f3b8674b1ff6beb455c
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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