Ammonium Chloride → HCID 86681719, compound

HRID 571311Notes

Reaction equation

HRID 571311 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C:7]2=[O:25])([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])[C:7]2=[O:25]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 41956059HCID 41956059, compound

Product 1

HCID 86681719HCID 86681719, compoundYield 94.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of benzyl 2-(5-nitro-1,3-dioxoisoindolin-2-yl)acetate (1.2 g, 3.528 mmol) in a mixture of ethanol (23 ml) and water (11.5 ml), iron powder (1.182 g, 21.16 mmol) and ammonium chloride (0.132 g, 2.468 mmol) were added, and the mixture was heated to reflux for 1 hour. The insoluble was filtered off and the filtrate was evaporated to dryness. The residue was dissolved in ethyl acetate and washed with water and brine (×3). The organic phase was dried over Na2SO4 and the solvent was removed to give benzyl 2-(5-amino-1,3-dioxoisoindolin-2-yl)acetate (1.035 g, 3.335 mmol, 94.5% yield, MS/ESI+ 310.9 [MH]+). This product was used in the following step without further purification.

Workup

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 1 hour
  4. filtrationThe insoluble was filtered off
  5. customthe filtrate was evaporated to dryness
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwashed with water and brine (×3)
  8. dry with materialThe organic phase was dried over Na2SO4
  9. customthe solvent was removed

Sources & evidence

ORD record
ord-711ccba0023f4997988b3b6d67deb40d
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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