Hydroquinone → [(S)-1-(4-Bromo-phenyl)-ethyl]-[2-(2-chloro-5-methoxy-4-nitro-phenyl)-ethyl]-amine

HRID 1019774Notes

Reaction equation

HRID 1019774 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[C:15]([O:21][CH3:22])=[CH:14][C:13]=1[CH:23]=[CH2:24].C1(C=CC(O)=CC=1)O>C(O)CCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:24][CH2:23][C:13]2[CH:14]=[C:15]([O:21][CH3:22])[C:16]([N+:18]([O-:20])=[O:19])=[CH:17][C:12]=2[Cl:11])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamineHCID 674659471-Chloro-4-methoxy-5-nitro-2-vinylbenzene

Product 1

HCID 67468993[(S)-1-(4-Bromo-phenyl)-ethyl]-[2-(2-chloro-5-methoxy-4-nitro-phenyl)-ethyl]-amineYield 57%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of (S)-1-(4-bromophenyl)ethylamine (0.94 g, 4.69 mmol), 1-chloro-4-methoxy-5-nitro-2-vinylbenzene (Example 50C) (0.5 g, 2.34 mmol) and quinol (0.1 g, 0.94 mmol) in n-butanol (6 mL) was heated to reflux for 18 hours. The reaction mixture was concentrated under reduced pressure then the residue partitioned between EtOAc (40 mL) and water (30 mL). The separated aqueous phase was extracted with EtOAc (3×40 mL), and then the combined organic extracts were washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using 0-1% MeOH in DCM to give the title compound (0.55 g, 57%).

Workup

  1. temperatureto reflux for 18 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue partitioned between EtOAc (40 mL) and water (30 mL)
  4. extractionThe separated aqueous phase was extracted with EtOAc (3×40 mL)
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography on silica gel using 0-1% MeOH in DCM

Sources & evidence

ORD record
ord-744c645ea7934a2580553d6b058f9f2f
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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