Ammonium Chloride → HCID 86675165, compound

HRID 1504653Notes

Reaction equation

HRID 1504653 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([C:24]([F:27])([F:26])[F:25])/[CH:11]=[CH:12]/[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([N:22]=O)[CH2:17][CH2:16]3)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].[NH4+].[Cl-]>CO.O.C(Cl)Cl.[Zn]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([C:24]([F:25])([F:26])[F:27])/[CH:11]=[CH:12]/[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([NH2:22])[CH2:17][CH2:16]3)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8]

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 86675166HCID 86675166, compound

Product 1

HCID 86675165HCID 86675165, compound

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To (E)-5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-1-nitrosoindoline (0.1 g, 0.2 mmol) in MeOH(10.0 mL) was added zinc powder (77.5 mg) and NH4Cl (36.9 mg, 0.69 mmol) in water (2.0 mL). The reaction mixture was stirred at ambient temperature for 3 h. The reaction mixture was diluted with CH2Cl2 and the CH2Cl2 layer was washed with water and brine solution. The separated CH2Cl2 layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude compound, which was purified by column chromatography (SiO2, 100-200 mesh; eluting with 2% ethyl acetate/petroleum ether) to afford the title compound as a light brown gummy material (0.08 g): ESIMS m/z 404.86 ([M+H]+).

Workup

  1. washthe CH2Cl2 layer was washed with water and brine solution
  2. dry with materialThe separated CH2Cl2 layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude compound, which
  5. customwas purified by column chromatography (SiO2, 100-200 mesh; eluting with 2% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-c4c8e63a34594cc3ab88da77a0023ee3
Source dataset
uspto-grants-2015_12
Patent number
US09215870B2

Reaction notes

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