Sodium Hydroxide → HCID 12049864, compound

HRID 1275673Notes

Reaction equation

HRID 1275673 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-])=O)[NH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[NH2:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[C:2]([Cl:1])=[CH:3][NH:4]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 120498633-CHLORO-4-NITRO-1H-INDOLE

Product 1

HCID 12049864HCID 12049864, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

Stannous chloride (4.59 g, 20.36 mmol) is added to a solution of 3-chloro-4-nitroindole in 50 mL of ethanol. The reaction is heated to 45° C. and stirred for 1.5 hours. The reaction is cooled to room temperature and treated with 1 M aqueous sodium hydroxide solution. This mixture is extracted with ethyl acetate. The combined organic extracts are dried over magnesium sulfate, filtered and the solvents removed by rotary evaporation. The crude residue is purified via silica gel column chromatography using 15% ethyl acetate/hexanes as the eluent. The appropriate fractions are combined and the solvents removed by rotary evaporation to yield 0.466 g of 4-amino-3-chloroindole as an off-white solid (55% yield).

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. extractionThis mixture is extracted with ethyl acetate
  3. dry with materialThe combined organic extracts are dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvents removed by rotary evaporation
  6. customThe crude residue is purified via silica gel column chromatography
  7. customthe solvents removed by rotary evaporation

Sources & evidence

ORD record
ord-fedf0ccefb104a83a82200d2df746f26
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

Loading…