Hydrochloric Acid → HCID 9816112, compound

HRID 2258562Notes

Reaction equation

HRID 2258562 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]([Cl:12])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:13]([O-])=O)[C:3]=1[OH:16].Cl.CO>CC(O)=O.[Pd]>[Cl:1][C:2]1[C:3]([OH:16])=[C:4]([NH2:13])[C:5](=[C:9]([Cl:12])[C:10]=1[CH3:11])[C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10587804HCID 10587804, compound

Product 1

HCID 9816112HCID 9816112, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

4,6-Dichloro-3-hydroxy-5-methyl -2nitrobenzoic acid (69 mg, 0.26 mmol) was dissolved in HOAc (10 mL), 10% Pd/C (10 mg) and concentrated HCl (33μ, 0.39 mmol) were added. Hydrogenation at room temperature and at atmospheric pressure for 2 h gave a slurry to which methanol (5 mL) was added and the catalyst was filtered off. Evaporation of the solvent, co-evaporation with toluene (10 mL) followed by vacuum-drying over KOH gave 63 mg of a crude product. Purification by flash column chromatography (SiO2), EtOAc-HOAc 45:1) yielded 55 mg of the title compound. Mp: 192° C. (dec); 1H NMR (DMSO-d6): δ 2.27 (s, 3H); 13C NMR (DMSO-d6): δ 167.43, 139.25, 136.01, 122.90, 121.26, 120.37, 116.89, 16.96;MS (EI, 70 eV): m/z (rel.int.) 237/235 (M+, 45/79), 219/217 (37/64), 191/189 (60/100).

Workup

  1. additionwas added
  2. filtrationthe catalyst was filtered off
  3. customEvaporation of the solvent, co-evaporation with toluene (10 mL)
  4. dry with materialby vacuum-drying over KOH
  5. customgave 63 mg of a crude product
  6. customPurification by flash column chromatography (SiO2), EtOAc-HOAc 45:1)

Sources & evidence

ORD record
ord-f98d714e73da45f1803b32f450fa6c73
Source dataset
uspto-grants-1997_08
Patent number
US05661183

Reaction notes

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