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

HRID 453860Notes

Reaction equation

HRID 453860 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][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>[Fe].C(O)C>[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][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 68498176tert-Butyl 2-(6-nitro-1H-indol-1-yl)acetate

Product 1

HCID 59473728tert-butyl 2-(6-amino-1H-indol-1-yl)acetateYield 61%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of tert-butyl 2-(6-nitro-1H-indol-1-yl)acetate (1.44 mmol, 1 equiv.), iron powder (5.76 mmol, 4 equiv.), ammonium chloride (4 equiv.) and ethanol (10 ml) was stirred for 4 h at boiling temperature. The reaction mixture was cooled to 25° C. and filtered over celite. The filtrate was concentrated, diluted with water (50 ml) and extracted with dichloromethane (3×20 ml). The combined organic phases were washed with water and sat. NaCl solution (in each case 10 ml), dried over Na2SO4 and concentrated under reduced pressure. For purification, the product was recrystallized from ethyl acetate/hexane. Yield: 61%

Workup

  1. filtrationfiltered over celite
  2. concentrationThe filtrate was concentrated
  3. additiondiluted with water (50 ml)
  4. extractionextracted with dichloromethane (3×20 ml)
  5. washThe combined organic phases were washed with water and sat. NaCl solution (in each case 10 ml),
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customFor purification
  9. customthe product was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-554e829f85664f6695bd87255bba531c
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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