Ammonium Chloride → HCID 59377963, compound

HRID 2065739Notes

Reaction equation

HRID 2065739 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH:5]([C:11]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:12]=1[Cl:20])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[Cl-].[NH4+]>CCO.O.[Fe]>[CH2:9]([O:8][C:6](=[O:7])[CH:5]([C:11]1[CH:16]=[C:15]([NH2:17])[CH:14]=[CH:13][C:12]=1[Cl:20])[C:4]([O:3][CH2:1][CH3:2])=[O:21])[CH3:10]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 59378014HCID 59378014, compound

Product 1

HCID 59377963HCID 59377963, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(2-chloro-5-nitro-phenyl)-malonic acid diethyl ester (2.3 g, 7.28 mmol) in EtOH (20 ml) and water (20 ml) was added Fe powder (2.0 g, 36.4 mmol) and ammonium chloride (2.0 g, 37.8 mmol). The mixture was heated at 100° C. for two hours. The mixture was filtered and the filtrate was concentrated to dryness under reduced pressure. The residue was partitioned between water and dichloromethane, and the organic layer was separated, washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the crude product by flash chromatography (hexanes:EtOAc 8:2) gave 1.35 g (65%) of 2-(5-amino-2-chloro-phenyl)-malonic acid diethyl ester as a yellow solid.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness under reduced pressure
  3. customThe residue was partitioned between water and dichloromethane
  4. customthe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure
  9. customPurification of the crude product by flash chromatography (hexanes:EtOAc 8:2)

Sources & evidence

ORD record
ord-ade641b6353d43328be0e28ff584f0aa
Source dataset
uspto-grants-2012_10
Patent number
US08288552B2

Reaction notes

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