Water → HCID 71278900, compound

HRID 1749762Notes

Reaction equation

HRID 1749762 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[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.[OH-].[Na+].O>CO>[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](/[CH:21]=[C:6]2/[C:7](=[O:11])[C:8]3[C:4]([CH2:5]/2)=[CH:3][C:2]([OH:1])=[CH:10][CH:9]=3)=[CH:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 10256Indole-3-CarboxaldehydeHCID 14798Sodium HydroxideHCID 2331475-Hydroxy-1-indanone

Product 1

HCID 71278900HCID 71278900, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 5-hydroxy-2,3-dihydro-1H-inden-1-one (0.30 g, 2.0 mmol) and 1H-indole-3-carboxaldehyde (0.32 g, 2.2 mmol) in methanol (10 mL) was added with 50% sodium hydroxide (0.34 mL), and the mixture was stirred at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, and then added with water, and the precipitated solid was collected by filtration, and washed with methanol to obtain (E)-2-[(1H-indol-3-yl)methylene]-5-hydroxy-2,3-dihydro-1H-inden-1-one (0.45 g, 83%).

Workup

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

Sources & evidence

ORD record
ord-02b781ca8b2641779e28e8d24461a268
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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