Hydrochloric Acid → HCID 71278696, compound

HRID 1749726Notes

Reaction equation

HRID 1749726 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.[CH3:12][C:13]1[NH:14][C:15]2[C:20]([C:21]=1[CH:22]=O)=[CH:19][CH:18]=[CH:17][CH:16]=2.Cl>C(O)C>[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])/[C:7](=[CH:22]/[C:21]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[NH:14][C:13]=3[CH3:12])/[O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 731663-Formyl-2-methylindoleHCID 2357176-Hydroxy-3-coumaranone

Product 1

HCID 71278696HCID 71278696, compoundYield 114.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 6-hydroxybenzofuran-3(2H)-one (0.50 g, 3.3 mmol) and 2-methyl-1H-indole-3-carboxaldehyde (0.58 g, 3.6 mmol) in ethanol (10 mL) was added with concentrated hydrochloric acid (1.0 mL), and the mixture was stirred at 75° C. for 2 hours. The reaction mixture was cooled to room temperature, and then the solid was collected by filtration, and washed with methanol to obtain (Z)-6-hydroxy-2-[(2-methyl-1H-indol-3-yl)methylene]benzofuran-3(2H)-one (1.1 g, 95%).

Workup

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

Sources & evidence

ORD record
ord-b3ad6afb876c4bc78e78940d91624edf
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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