Ammonium Chloride → Ethyl 2-(6-amino-1H-indol-1-yl)acetate

HRID 453866Notes

Reaction equation

HRID 453866 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>[Fe].C(O)C.O>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 43308826Ethyl 2-(6-nitro-1H-indol-1-yl)acetate

Product 1

HCID 16731704Ethyl 2-(6-amino-1H-indol-1-yl)acetateYield 55%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of ethyl 2-(6-nitro-1H-indol-1-yl)acetate (20.96 mmol, 1 equiv.), iron powder (83.8 mmol, 4 equiv.), ammonium chloride (83.87 mmol, 1 equiv.) and ethanol/water (2.5:1, 56 ml) was stirred for 2 h at boiling temperature. The reaction mixture was cooled to 25° C. and filtered over celite. The filtrate was diluted with ethyl acetate and water, the phases were separated, and the organic phase was washed with sodium hydrogen carbonate solution and sat. NaCl solution, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (15% ethyl acetate in hexane). Yield: 55%

Workup

  1. filtrationfiltered over celite
  2. additionThe filtrate was diluted with ethyl acetate and water
  3. customthe phases were separated
  4. washthe organic phase was washed with sodium hydrogen carbonate solution and sat. NaCl solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography (15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-43ed7fd540c340b1b81425a2ac8698e6
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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