Hydrochloric Acid → HCID 1777704, compound

HRID 1749696Notes

Reaction equation

HRID 1749696 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[CH:3]=1.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH:21]=O)=[CH:13]1.Cl>C(O)C>[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](/[CH:21]=[C:7]2\[O:8][C:4]3[CH:3]=[C:2]([OH:1])[CH:11]=[CH:10][C:5]=3[C:6]\2=[O:9])=[CH:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10256Indole-3-CarboxaldehydeHCID 2357176-Hydroxy-3-coumaranone

Product 1

HCID 1777704HCID 1777704, compoundYield 105.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

The synthesis was performed with reference to the known literature (International Patent Publication WO1998/30556). A solution of 6-hydroxybenzofuran-3(2H)-one (2.0 g, 13 mmol) and 1H-indole-3-carboxaldehyde (2.3 g, 16 mmol) in ethanol (100 mL) was added with concentrated hydrochloric acid (10 mL), and the mixture was stirred at 75° C. for 5 hours. The reaction mixture was cooled to room temperature, and then the solid was collected by filtration, and washed with methanol and water to obtain (Z)-2-[(1H-indol-3-yl)methylene]-6-hydroxybenzofuran-3(2H)-one (3.8 g, 100%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe solid was collected by filtration
  3. washwashed with methanol and water

Sources & evidence

ORD record
ord-a2560947ebf64e2d843fba50b0efca3e
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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