Sodium Hydroxide → 2-Fluoro-4-chloro-5-(3-methylcyclopentyl)oxyaniline

HRID 21477Notes

Reaction equation

HRID 21477 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([O:11][CH:12]2[CH2:16][CH2:15][CH:14]([CH3:17])[CH2:13]2)=[CH:6][C:5]=1[NH:18]C(=O)OC>C(O)C>[F:3][C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([O:11][CH:12]2[CH2:16][CH2:15][CH:14]([CH3:17])[CH2:13]2)=[CH:6][C:5]=1[NH2:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19374472methyl N-{2-fluoro-4-chloro-5-(3-methylcyclopentyl)oxyphenyl}carbamate

Product 1

HCID 152793912-Fluoro-4-chloro-5-(3-methylcyclopentyl)oxyanilineYield 63.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Then, ethyl alcohol (20 ml) and a 2N aqueous solution of sodium hydroxide (30 ml) were added to the resulting methyl N-{2-fluoro-4-chloro-5-(3-methylcyclopentyl)oxyphenyl}carbamate (3.45 g, 11.4 mmol), followed by stirring for 3 hours under refluxing. After completion of the reaction, the reaction mixture was extracted with ethyl acetate (50 ml×3 times). The organic layer was washed with a saturated aqueous sodium chloride solution, dried, and the solvent was distilled off under reduced pressure to obtain 2-fluoro-4-chloro-5-(3-methylcyclopentyl)oxyaniline (1.77 g, 7.26 mmol, 63.64 yield). 1H-NMR Spectrum (CDCl3, TMS, ppm): δ1.02 and 1.10 (total 3H, d, J=6.0 Hz), 1.22-2.58 (7H, m), 3.75 (2H, br, s), 4.65 (1H, m), 6.33 (1H, d, JHF =8.0 Hz), 6.98 (1H, d, JHF =10.0 Hz).

Workup

  1. temperatureunder refluxing
  2. customAfter completion of the reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate (50 ml×3 times)
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. customdried
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-678f5628079e4fbc98be4eafe82a5ab1
Source dataset
uspto-grants-1995_06
Patent number
US05424277

Reaction notes

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