Sodium Hydroxide → HCID 17954765, compound

HRID 1929318Notes

Reaction equation

HRID 1929318 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[C:14]([N+:21]([O-:23])=[O:22])[CH:15]=[CH:16][C:17]=3[O:19][CH3:20])[CH:12]=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>CO.O>[CH3:20][O:19][C:17]1[CH:16]=[CH:15][C:14]([N+:21]([O-:23])=[O:22])=[C:13]2[C:18]=1[NH:10][CH:11]=[CH:12]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 152863207-Methoxy-4-nitro-1-(phenylsulfonyl)indole

Product 1

HCID 17954765HCID 17954765, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-benzenesulfonyl-7-methoxy-4-nitro-1H-indole (R) (1 eq) in methanol was added a solution of sodium hydroxide (5 eq) in water. The solution was heated to reflux for 3 hrs. Methanol was removed under reduced pressure then water and ethyl acetate were added. The ethyl acetate layer separated and washed repeatedly (3×) with water. The ethyl acetate layer was concentrated and evaporated to dryness to produce the desired product.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 3 hrs
  3. customMethanol was removed under reduced pressure
  4. additionwater and ethyl acetate were added
  5. customThe ethyl acetate layer separated
  6. washwashed repeatedly (3×) with water
  7. concentrationThe ethyl acetate layer was concentrated
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-c1fcef5ad04b4070a23a8191630947c4
Source dataset
uspto-grants-2012_05
Patent number
US08188075B2

Reaction notes

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