Ammonium Chloride → HCID 86675165, compound

HRID 1503699Notes

Reaction equation

HRID 1503699 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 methanol (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 RT for 3 h. The reaction mixture was diluted with DCM and the DCM layer was washed with water and brine solution. The separated DCM 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 DCM layer was washed with water and brine solution
  2. dry with materialThe separated DCM 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-52b5e83838174aa5ab32eae6a4d59664
Source dataset
uspto-grants-2015_12
Patent number
US09212164B2

Reaction notes

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