Sulfuric Acid → 8-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indole

HRID 1401393Notes

Reaction equation

HRID 1401393 reaction equation
S(=O)(=O)(O)O.Cl.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14]N)=[CH:10][CH:9]=1.[CH3:16][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C:18]1=O>O1CCOCC1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]2[NH:14][C:20]3[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][C:19]=3[C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 13603N-Methyl-2-piperidoneHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)

Product 1

HCID 196158-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sulfuric acid (3.5 mL) was added to a solution of 4-chlorophenylhydrazine hydrochloride (2.0 g, 11.2 mmol) in dioxane (50 mL), and stirred for 5 min. at RT. N-methyl piperidone (0.76-1.4 equiv.) was added and the mixture was heated at 80° C. for 2 h. After reaction completion as determined by thin layer chromatography (TLC), the reaction mixture was concentrated to approximately 20 mL under reduced pressure and basified to pH 10 using a 10% aqueous KOH solution. The reaction product was extracted with EtOAc (3×50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure using a rotary evaporator to obtain the product (1.3 g) as a brown solid. 1H NMR (CDCl3, freebase) δ (ppm): 7.40 (s, 1H), 7.20-7.10 (d, 1H), 7.10-7.00 (d, 1H), 3.60 (s, 2H), 2.90 (s, 4H), 2.60 (s, 3H).

Workup

  1. temperaturethe mixture was heated at 80° C. for 2 h
  2. customAfter reaction completion
  3. concentrationthe reaction mixture was concentrated to approximately 20 mL under reduced pressure and basified to pH 10
  4. extractionThe reaction product was extracted with EtOAc (3×50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customa rotary evaporator

Sources & evidence

ORD record
ord-aa0c625d84244b66a504e74c4967fa7e
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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