Ammonium Chloride → HCID 86681665, compound

HRID 571251Notes

Reaction equation

HRID 571251 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH2:8][CH2:7]2)([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)[N:9]([CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH2:8][CH2:7]2

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86681664HCID 86681664, compound

Product 1

HCID 86681665HCID 86681665, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of benzyl 2-(5-nitroindolin-1-yl)acetate (0.700 g, 2.241 mmol) in a mixture of ethanol (20 ml) and water (10 ml), iron powder (0.751 g, 13.45 mmol) and ammonium chloride (0.084 g, 1.569 mmol) were added, and the resulting mixture was heated to reflux for 1 hour and 15 minutes. The insoluble was filtered off, and the filtrate was concentrated under vacuum. The residue was dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulfate and evaporated to dryness to give benzyl 2-(5-aminoindolin-1-yl)acetate (0.626 g, 2.217 mmol, 99% yield). MS/ESI+ 283.0 [MH]+.

Workup

  1. additionwere added
  2. temperaturethe resulting mixture was heated
  3. temperatureto reflux for 1 hour and 15 minutes
  4. filtrationThe insoluble was filtered off
  5. concentrationthe filtrate was concentrated under vacuum
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwashed with water and brine
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-7ad9b489db434d07bfde9ae2724eec73
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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