Ammonium Chloride → HCID 67469271, compound

HRID 1019735Notes

Reaction equation

HRID 1019735 reaction equation
[C:1]([O:5][C:6](=[O:28])[N:7]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:19]=1[Cl:27])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-]>CO.[Zn]>[C:1]([O:5][C:6](=[O:28])[N:7]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:19]=1[Cl:27])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67465963HCID 67465963, compound

Product 1

HCID 67469271HCID 67469271, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of [2-(2-chloro-4-nitro-phenyl)ethyl]-(4-fluoro-benzyl)-carbamic acid tert-butyl ester (0.6 g, 1.4 mmol) in methanol (18 mL) was added a saturated solution of NH4Cl (18 mL), followed by zinc powder (0.41 g, 7.3 mmol) and the reaction mixture was heated at 45° C. for 1 hour. The reaction mixture was cooled to RT, filtered and EtOAc (60 mL) and water (100 mL) were added to the filtrate and the mixture was stirred for 15 minutes. The separated organic phase was washed with water (80 mL), brine (80 mL), dried (Na2SO4) and the solvents removed under reduced pressure to afford the title compound (0.49 g, 88%).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationfiltered
  3. additionEtOAc (60 mL) and water (100 mL) were added to the filtrate
  4. washThe separated organic phase was washed with water (80 mL), brine (80 mL)
  5. dry with materialdried (Na2SO4)
  6. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-e64a6f0d97a94c9b8890c8fd947f1344
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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