Hydrochloric Acid → HCID 53967432, compound

HRID 259937Notes

Reaction equation

HRID 259937 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N+:12]([O-])=O)[C:3]=1[O:15][CH3:16].Cl>CO.[Pd]>[Cl:1][C:2]1[C:3]([O:15][CH3:16])=[C:4]([CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1)[NH2:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53847941HCID 53847941, compound

Product 1

HCID 53967432HCID 53967432, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Chloro-2-methoxy-3-nitro-5-trifluoromethylbenzene (3.46 g, 13.5 mmol) was dissolved in MeOH (74 mL). Hydrochloric acid (2M, 13 mL, 26 mmol) and Pd/C (10%, 0.44 g) was added. Hydrogenation at atmospheric pressure and at room temperature for 1 h 30 min, filtration and evaporation of the solvent gave a crude product. Purification by flash chromatography (SiO2, CH2Cl2 -hexane 1:2 followed by EtOAc-NH3 100:0.1) yielded the title compound (3.08 g) as an oil. 1H NMR (CDCl3): 7.00 (J 1.8 Hz, 1H), 6.85 (d, J=1.95 Hz, 1H), 4.11 (br s, 2H), 3.87 (s, 3H). MS (EI, 70 eV): m/z (rel. int.) 227/225 (M+, 17/58).

Workup

  1. filtrationHydrogenation at atmospheric pressure and at room temperature for 1 h 30 min, filtration and evaporation of the solvent
  2. customgave a crude product
  3. customPurification by flash chromatography (SiO2, CH2Cl2 -hexane 1:2 followed by EtOAc-NH3 100:0.1)

Sources & evidence

ORD record
ord-9ede22c500bc43de88eb4af797d9e37a
Source dataset
uspto-grants-1996_06
Patent number
US05523475

Reaction notes

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