HCID 70665120, compound → HCID 67202892, compound

HRID 1472507Notes

Reaction equation

HRID 1472507 reaction equation
[CH:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]([C:14]3[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=3[C:16](OC)=[O:17])[C:5]=2[CH:4]=[CH:3][N:2]=1>C(O)(=O)C.S(=O)(=O)(O)O>[CH:4]1[C:5]2[N:6]3[C:7]4[C:12]([C:13]=2[CH:1]=[N:2][CH:3]=1)=[CH:11][CH:10]=[CH:9][C:8]=4[C:16](=[O:17])[C:15]1[C:14]3=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 1

HCID 70665120HCID 70665120, compound

Product 1

HCID 67202892HCID 67202892, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

15.1 g (50 mmol) of methyl 2-pyrido[4,3-b]indol-5-ylbenzoate are suspended in a mixture of 200 ml of glacial acetic acid and 5 ml of concentrated sulfuric acid. The suspension is heated under reflux for 5 h, the acetic acid is then removed in vacuo, and the residue is taken up in 500 ml of dichloromethane and neutralised using 1 N sodium hydroxide solution. The organic phase is separated off, dried over magnesium sulfate and evaporated in vacuo. The residue is taken up in 30 ml of ethyl acetate, and 100 ml of ethanol are slowly added at elevated temperature. After cooling, the precipitated solid is filtered off with suction, washed three times with 50 ml of ethanol and dried in vacuo (p=0.1 mbar, T=60° C.). Yield: 10.5 g (39 mmol), 78%; purity: 97% (1H-NMR).

Workup

  1. temperatureThe suspension is heated
  2. temperatureunder reflux for 5 h
  3. customthe acetic acid is then removed in vacuo
  4. customThe organic phase is separated off
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. addition100 ml of ethanol are slowly added at elevated temperature
  8. temperatureAfter cooling
  9. filtrationthe precipitated solid is filtered off with suction
  10. washwashed three times with 50 ml of ethanol
  11. customdried in vacuo (p=0.1 mbar, T=60° C.)

Sources & evidence

ORD record
ord-849dcf57f85440779c7690bbbfa0b0d2
Source dataset
uspto-grants-2015_04
Patent number
US09012599B2

Reaction notes

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