ethyl 2-(5-nitro-1H-indol-2-yl)propanoate → ethyl 2-(5-amino-1H-indol-2-yl)propanoate

HRID 1847502Notes

Reaction equation

HRID 1847502 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7]2)([O-])=O.O.O.[Sn](Cl)(Cl)(Cl)Cl>C(O)C.C(OCC)(=O)C.O.C([O-])(O)=O.[Na+]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7]2

Participants

7

Reactant 2

HCID 59129193ethyl 2-(5-nitro-1H-indol-2-yl)propanoateHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 59129453ethyl 2-(5-amino-1H-indol-2-yl)propanoateYield 99.7%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of ethyl 2-(5-nitro-1H-indol-2-yl)propanoate (0.10 g, 0.38 mmol) in ethanol (4 mL) was added tin chloride dihydrate (0.431 g, 1.91 mmol). The mixture was heated in the microwave at 120° C. for 1 h. The mixture was diluted with ethyl acetate before water and saturated aqueous NaHCO3 were added. The reaction mixture was filtered through a plug of celite using ethyl acetate. The organic layer was separated from the aqueous layer. The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure to give ethyl 2-(5-amino-1H-indol-2-yl)propanoate (0.088 g, 99%).

Workup

  1. additionwere added
  2. filtrationThe reaction mixture was filtered through a plug of celite
  3. customThe organic layer was separated from the aqueous layer
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-96e7c911abdd482d9581f3178ef06edd
Source dataset
uspto-grants-2015_02
Patent number
US08952050B2

Reaction notes

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