Hydrazine hydrate (1:1) → 4-Amino-3-methoxy-N,N-dimethylbenzenesulfonamide

HRID 523085Notes

Reaction equation

HRID 523085 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[C:12]1[CH:17]=[CH:16][C:15]([S:18]([N:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])=[CH:14][C:13]=1[O:24][CH3:25].O.NN>CO>[NH2:3][C:12]1[CH:17]=[CH:16][C:15]([S:18]([N:21]([CH3:22])[CH3:23])(=[O:19])=[O:20])=[CH:14][C:13]=1[O:24][CH3:25]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 89995761HCID 89995761, compound

Product 1

HCID 225063424-Amino-3-methoxy-N,N-dimethylbenzenesulfonamideYield 34.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(1,3-Dioxoisoindolin-2-yl)-3-methoxy-N,N-dimethylbenzenesulfonamide (Preparation 105, 50 mg, 0.139 mmol) was suspended in MeOH (6 mL) and hydrazine hydrate (1 mL) was added. The resulting solution was stirred at room temperature for 2 hours before concentrating in vacuo. The residue was purified using Biotage silica gel column chromatography eluting with 50% EtOAc in cyclohexane to give the title compound as white solid (11 mg, 34%).

Workup

  1. concentrationbefore concentrating in vacuo
  2. customThe residue was purified
  3. washeluting with 50% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-969ae64bbc064ce6b7d9259e0c6eb992
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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