Sodium Hydroxide → 4-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamine

HRID 128542

Reaction equation

HRID 128542 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][CH2:14][CH2:13]2)=[CH:6][C:5]=1[NH:17]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][CH2:14][CH2:13]2)=[CH:6][C:5]=1[NH2:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15766845methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate

Product 1

HCID 152793894-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamineYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

Ethyl alcohol (30 ml) and a 2N aqueous solution of sodium hydroxide (50 ml) were added to methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate obtained above, and the mixture was stirred For 4 hours while heating on an oil bath at 110° C. After completion of the reaction, the solvent was distilled off, and the residue was extracted with ethyl acetate (100 ml×3 times). The organic layer was washed with a saturated aqueous solution of sodium chloride, dried, and the solvent was distilled off under reduced pressure to obtain oily 2-fluoro-4-chloro-5-cyclopentyloxyaniline (4.38 g, 19.0 mmol, 95.0% yield). The spectral data and the like are as shown in Reference Example 1.

Workup

  1. customobtained above, and the mixture
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off
  4. extractionthe residue was extracted with ethyl acetate (100 ml×3 times)
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  6. customdried
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-70181d034620481fa81416fc7dfe9ecb
Source dataset
uspto-grants-1995_11
Patent number
US05464811

Linked notes

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