Acetic Acid → HCID 69263578, compound

HRID 888117Notes

Reaction equation

HRID 888117 reaction equation
[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=2)[C:7]([CH3:18])([CH3:17])[CH2:6]1)(=[O:4])=[O:3].CC(O)=O>C1COCC1.[Zn]>[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH2:14])[CH:12]=2)[C:7]([CH3:18])([CH3:17])[CH2:6]1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 69264583HCID 69264583, compound

Product 1

HCID 69263578HCID 69263578, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-Methanesulfonyl-3,3-dimethyl-6-nitro-2,3-dihydro-1H-indole (0.88 mg, 3.22 mmol) and AcOH (3.5 mL) in THF (100 mL) was added Zinc dust (14 g, 247 mmol) by small portion. The resulting mixture was stirred at RT for 2 h and was filtered over a Celite® pad. Solvent was evaporated and residue was diluted in CH2Cl2 and washed with NaOH 1M. The resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo to give 1-Methanesulfonyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-ylamine.

Workup

  1. filtrationwas filtered over a Celite® pad
  2. customSolvent was evaporated
  3. additionresidue was diluted in CH2Cl2
  4. washwashed with NaOH 1M
  5. dry with materialThe resulting organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a02c4b7f66045619c2e0e758af883cb
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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