Hydrochloric Acid → 2'-Fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-amine

HRID 1049422Notes

Reaction equation

HRID 1049422 reaction equation
C1(C(C2C=CC=CC=2)=[N:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=3[F:23])=[C:11]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:10]=2)C=CC=CC=1.Cl.[OH-].[Na+]>C1COCC1>[F:23][C:16]1[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:15]=1[C:12]1[CH:13]=[CH:14][C:9]([NH2:8])=[CH:10][C:11]=1[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 117760119N-(diphenylmethylene)-2'-fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-amine

Product 1

HCID 1177600312'-Fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-amineYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of a mixture (1.90 g) of N-(diphenylmethylene)-2′-fluoro-5′-methoxy-2-neopentyl-[1,1′-biphenyl]-4-amine in THF (42 mL) was added 3N hydrochloric acid (14.0 mL) at 0° C., and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added 8N aqueous sodium hydroxide solution at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (970 mg) as a pale-yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-afdad2da0a9040948eb15b399ed73f30
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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