Hydrochloric Acid → 5-chloro-3-methyl-2-pyridin-3-yl-1H-indole hydrochloride

HRID 1661536Notes

Reaction equation

HRID 1661536 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[C:11]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)(=O)[CH2:12][CH3:13].Cl>C(O)C>[ClH:2].[Cl:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][C:11]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=[C:12]2[CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 740741-(3-Pyridyl)propan-1-one

Product 1

HCID 445539625-chloro-3-methyl-2-pyridin-3-yl-1H-indole hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Chloro-3-methyl-2-pyridin-3-yl-1H-indole hydrochloride is synthesized based on the method described in U.S. Pat. No. 3,468,894. (4-Chloro-phenyl)-hydrazine hydrochloride (3.0 g, 16.8 mmol) and 3-propionylpyridine (2.4 g, 17.6 mmol) in ethanol (45 mL) is heated to reflux for 6 h. The mixture is then cooled to room temperature and added to HCl (4M in 1,4-dioxane, 17.6 mL). The resulting mixture is heated to reflux for 24 h. The mixture is then cooled to room temperature and the yellow precipitate is filtered and washed with methanol (10 mL) three times to give 5-chloro-3-methyl-2-pyridin-3-yl-1H-indole hydrochloride as a yellow solid. MS (ESI) m/z 243.0 and 244.9 (M+H)+.

Workup

  1. custom5-Chloro-3-methyl-2-pyridin-3-yl-1H-indole hydrochloride is synthesized
  2. temperatureto reflux for 6 h
  3. temperatureThe resulting mixture is heated
  4. temperatureto reflux for 24 h
  5. temperatureThe mixture is then cooled to room temperature
  6. filtrationthe yellow precipitate is filtered
  7. washwashed with methanol (10 mL) three times

Sources & evidence

ORD record
ord-ff442739462a458a854314722e1f15c8
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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