Hydrochloric Acid → Ethyl 3-(4-chlorophenyl)-1h-indole-2-carboxylate

HRID 430646Notes

Reaction equation

HRID 430646 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[C:16]1([NH:22]N)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)C.Cl>S(=O)(=O)(O)O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:22][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7516PhenylhydrazineHCID 2736395Ethyl 3-(4-chlorophenyl)-2-oxopropanoate

Product 1

HCID 18351540Ethyl 3-(4-chlorophenyl)-1h-indole-2-carboxylateYield 12%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of Example 52A (4.75 g, 21.0 mmol) and phenyl hydrazine (2.07 mL, 21.0 mmol) was treated with concentrated sulfuric acid (5 drops), heated to 120° C. for 15 minutes, cooled to room temperature, treated with ethanol (25 mL), treated with bubbling HCl gas for 2 minutes, and heated to reflux for 1 hour. The mixture was poured into water (30 mL) and extracted with diethyl ether. The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated. The concentrate was recrystallized from ethanol to provide 750 mg (12%) of the desired product.

Workup

  1. temperaturecooled to room temperature
  2. temperatureheated
  3. temperatureto reflux for 1 hour
  4. extractionextracted with diethyl ether
  5. washThe combined extracts were washed with water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe concentrate was recrystallized from ethanol

Sources & evidence

ORD record
ord-bd2de23d808e4c7480e4110de6afcda0
Source dataset
uspto-grants-2001_11
Patent number
US06323228B1

Reaction notes

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