Ethyl Acetate → HCID 22277806, compound

HRID 2055330Notes

Reaction equation

HRID 2055330 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[S:7][C:6]=2[CH:5]=[CH:4][C:3]=1[N+:15]([O-])=O.CCOC(C)=O>C(O)C.[Pd]>[NH2:15][C:3]1[CH:4]=[CH:5][C:6]2[S:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[C:10]=2[C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 222777981-Methyl-2-nitrodibenzothiophene

Product 1

HCID 22277806HCID 22277806, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-Methyl-2-nitrodibenzothiophene (Method 11; 0.855 g, 3.52 mmol) was stirred in ethanol (50 ml) and EtOAc (50 ml) under an argon atmosphere. 10% Palladium on carbon (0.09 g) was added to the solution and the reaction mixture was stirred under a hydrogen atmosphere at room temperature for 3 h. The mixture was filtered through diatomaceous earth and washed with EtOAc before the filtrate was evaporated in vacuo. The crude product was purified by flash chromatography eluting with 50% DCM/iso-hexane-DCM. Evaporation of the appropriate fractions left the product as a colourless solid. NMR: 8.39 (m, 1H), 7.92 (m, 1H), 7.50 (m,1H), 7.42 (m, 2H), 6.92 (d, 1H), 4.98 (brs, 2H), 2.60 (s, 3H); m/z 215.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. washwashed with EtOAc before the filtrate
  3. customwas evaporated in vacuo
  4. customThe crude product was purified by flash chromatography
  5. washeluting with 50% DCM/iso-hexane-DCM
  6. customEvaporation of the appropriate fractions
  7. waitleft the product as a colourless solid

Sources & evidence

ORD record
ord-f27db409cd4d46639a3c45ac006f22f6
Source dataset
uspto-grants-2008_02
Patent number
US07332492B2

Reaction notes

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