HCID 59129524, compound → HCID 59129294, compound

HRID 1991744Notes

Reaction equation

HRID 1991744 reaction equation
[CH3:1][C:2]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([N+:15]([O-])=O)=[CH:10][CH:9]=2)([CH3:5])[CH2:3][OH:4].O.O.[Sn](Cl)(Cl)(Cl)Cl>C(O)C.C(OCC)(=O)C.O>[NH2:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:2]([CH3:5])([CH3:1])[CH2:3][OH:4])=[CH:14]2

Participants

6

Reactant 2

HCID 59129524HCID 59129524, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 59129294HCID 59129294, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-methyl-2-(5-nitro-1H-indol-2-yl)propan-1-ol (0.094 g, 0.40 mmol) in ethanol (4 mL) was added tin chloride dihydrate (0.451 g, 2.0 mmol). The mixture was heated in the microwave at 120° C. for 1 h. The mixture was diluted with ethyl acetate and water before being quenched with saturated aqueous NaHCO3. The reaction mixture was filtered through a plug of celite using ethyl acetate. The organic layer was separated from the aqueous layer, dried over Na2SO4, filtered and evaporated under reduced pressure to give 2-(5-amino-1H-indol-2-yl)-2-methylpropan-1-ol (0.080 g, 98%).

Workup

  1. custombefore being quenched with saturated aqueous NaHCO3
  2. filtrationThe reaction mixture was filtered through a plug of celite
  3. customThe organic layer was separated from the aqueous layer
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ca893fb41cca48dbb9cedacc72461d89
Source dataset
uspto-grants-2010_01
Patent number
US07645789B2

Reaction notes

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