4-Methylphenylhydrazine monohydrochloride → ethyl 8-methyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

HRID 62149

Reaction equation

HRID 62149 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.[C:11]([N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1)([O:13][CH2:14][CH3:15])=[O:12]>CCO>[CH3:10][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:19]3[CH2:20][CH2:21][N:16]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:17][C:18]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 125044-Methylphenylhydrazine monohydrochlorideHCID 34767Ethyl 4-oxo-1-piperidinecarboxylate

Product 1

HCID 2937007ethyl 8-methyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following a literature procedure (Harbert et al., J. Med. Chem. 1980, 23, 635-643) p-tolylhydrazine hydrochloride (0.500 g, 3.15 mmol) and 1-carbethoxy-4-piperidone (0.18 mL, 1.17 mmol) were suspended in EtOH (0.880 mL) and heated to reflux for 2 hours. The reaction mixture was removed from heat and allowed to stand overnight at ambient temperature. The resulting mixture was filtered and washed with 50% aqueous EtOH to afford the desired product as a beige powder (259 mg, 86%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. customThe reaction mixture was removed
  4. temperaturefrom heat
  5. filtrationThe resulting mixture was filtered
  6. washwashed with 50% aqueous EtOH

Sources & evidence

ORD record
ord-eeda6d7f8cf34dcd8cb745bacce6b560
Source dataset
uspto-grants-2016_09
Patent number
US09446022B2

Linked notes

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