Ethyl Acetate → HCID 59444138, compound

HRID 1968976Notes

Reaction equation

HRID 1968976 reaction equation
[CH3:1][C:2]1[C:3]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([OH:8])[CH:7]=1.CCOC(C)=O>CCO>[NH2:9][C:5]1[CH:4]=[C:3]([S:12]([CH3:15])(=[O:14])=[O:13])[C:2]([CH3:1])=[CH:7][C:6]=1[OH:8]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 59444087HCID 59444087, compound

Product 1

HCID 59444138HCID 59444138, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Methyl-4-(methylsulfonyl)-2-nitrophenol (D86, 103 mg, 0.45 mmol) was dissolved in EtOH:EtOAc (20 mL, 1:1) and was reduced using an H-Cube (full H2 mode, 25° C., 1 mL/min). The reaction was concentrated by rotary evaporation and the crude residue was purified via flash column chromatography (silica, DCM to 0.5% NH3/9.5% MeOH/90% DCM) to give 2-amino-5-methyl-4-(methylsulfonyl)phenol (D87, 48 mg, 41%) as a yellow solid.

Workup

  1. customan H-Cube (full H2 mode, 25° C., 1 mL/min)
  2. concentrationThe reaction was concentrated by rotary evaporation
  3. customthe crude residue was purified via flash column chromatography (silica, DCM to 0.5% NH3/9.5% MeOH/90% DCM)

Sources & evidence

ORD record
ord-6969d039ad3540e3ac6255cbe8bc5012
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

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