Reaction #1929007

ord-6b6a8d56fcc64573a14ccd70eed873f9

Reaction equation

c1ccc2[nH]ccc2c1
indole
O=S([O-])O.[Na+]
sodium bisulfite
→
O=S(=O)([O-])c1cc2ccccc2[nH]1.[Na+]
sodium indole-2-sulfonate

Reactants

c1ccc2[nH]ccc2c1
indole
O=S([O-])O.[Na+]
sodium bisulfite

Reagents

None

Solvents

CCO
ethanol
O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherthe synthesis of 5,6,7-trichlorogramine
  2. 2
    FiltrationThe solid precipitate is filtered
  3. 3
    Washwashed with ether
  4. 4
    Otherdried

Procedure

FIG. 1b shows the synthesis of 5,6,7-trichlorogramine. A solution of indole (AA) in ethanol is added to a solution of sodium bisulfite in water. The mixture is stirred at room temperature for 12 hrs. The solid precipitate is filtered, washed with ether, and dried to yield sodium indole-2-sulfonate (BB) as a white solid. The sodium indole-2-sulfonate product (BB) is used in the next step without further purification. MP>320° C.; IR (KBr, cm−1) 3470, 3250, 1650, 1600, 1490, 1460, 1210, 1170, 1040, 760, 750.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08945397B2uspto-grants-2015_02