Hydrochloric Acid → trans-4-[1-methyl-2-phenyl-1H-indol-3-yl]-3-buten-2-one

HRID 547979

Reaction equation

HRID 547979 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CO[CH:19](OC)[CH2:20][C:21](=[O:23])[CH3:22].Cl>C(O)(=O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](/[CH:19]=[CH:20]/[C:21](=[O:23])[CH3:22])=[C:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 770951-Methyl-2-phenylindoleHCID 2285484,4-Dimethoxy-2-butanone

Product 1

HCID 11254370trans-4-[1-methyl-2-phenyl-1H-indol-3-yl]-3-buten-2-oneYield 89%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.07 g of 1-methyl-2-phenyl-1H-indole, 1.32 g of 1,1-dimethoxy-3-butanone and 12 mL of acetic acid were mixed, then, 313 mg of 35 wt % hydrochloric acid was added into the mixture at room temperature, the added mixture was stirred for about 14 hours at the same temperature to cause a reaction. At a time point about 10 minutes after starting of stirring and reaction, blue solid precipitated to render stirring difficult. Therefore, 8 mL of acetic acid was added. After completion of the reaction, 60 mL of water was added dropwise, and the precipitated crystals were filtrated. The crystals were washed with 10 vol % methanol/water, then, dried to obtain 2.44 g of trans-4-[1-methyl-2-phenyl-1H-indol-3-yl]-3-buten-2-one (blue green solid). Yield: 89%.

Workup

  1. customa reaction
  2. customAt a time point about 10 minutes
  3. stirringof stirring
  4. customreaction, blue solid
  5. customprecipitated
  6. stirringto render stirring difficult
  7. additionTherefore, 8 mL of acetic acid was added
  8. customAfter completion of the reaction, 60 mL of water
  9. additionwas added dropwise
  10. filtrationthe precipitated crystals were filtrated
  11. washThe crystals were washed with 10 vol % methanol/water
  12. customdried

Sources & evidence

ORD record
ord-0f619653e2ff42dfa5ec1ae7726cc3f0
Source dataset
uspto-grants-2011_05
Patent number
US07939674B2

Linked notes

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