Acetic Acid → HCID 86701530, compound

HRID 2173963Notes

Reaction equation

HRID 2173963 reaction equation
[CH3:1][C:2]1[C:3]([N+:22]([O-])=O)=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.CCOC(C)=O.CC(O)=O>CO.[Zn]>[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]2[N:7]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:6]=[CH:5][C:4]=2[C:3]=1[NH2:22]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 86701531HCID 86701531, compound

Product 1

HCID 86701530HCID 86701530, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5,7-dimethyl-4-nitro-1-tosyl-1H-indole (17 g, 49.4 mmol) in MeOH (50 mL)/EtOAc (300 mL) was added Zn (16.1 g, 247 mmol). The suspension was cooled down to 0° C. To the suspension was added dropwise AcOH (30 mL) over 30 min, and then the mixture was stirred at 0° C. for 0.5 h. The flask was removed from the ice bath, and the mixture left stirring at room temperature for 18.5 h. The reaction mixture was poured into a mixture of Celite®/5% aq. NaHCO3/EtOAc, and then the basic mixture was vigorously stirred for 0.5 h. The mixture was filtered through Celite®. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic phase was washed with 5% aq. NaHCO3, H2O, and brine, dried over Na2SO4, and then filtered. Concentration of the filtrate gave the title compound, without need of further purification. MS (ESI+) m/z 315.1 (M+H).

Workup

  1. customThe flask was removed from the ice bath
  2. waitthe mixture left
  3. stirringstirring at room temperature for 18.5 h
  4. additionThe reaction mixture was poured into a mixture of Celite®/5% aq. NaHCO3/EtOAc
  5. stirringthe basic mixture was vigorously stirred for 0.5 h
  6. filtrationThe mixture was filtered through Celite®
  7. customThe layers were separated
  8. extractionthe aqueous layer was extracted with EtOAc
  9. washThe combined organic phase was washed with 5% aq. NaHCO3, H2O, and brine
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered

Sources & evidence

ORD record
ord-d6ae4a59199e4e6a85487f99652968da
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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