Formaldehyde → HCID 71278620, compound

HRID 1749704Notes

Reaction equation

HRID 1749704 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1.[CH3:22][N:23]([CH3:29])[CH2:24][CH2:25][CH2:26][NH:27][CH3:28].[CH2:30]=O>C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[C:20]([CH2:22][N:23]([CH2:24][CH2:25][CH2:26][N:27]([CH3:30])[CH3:28])[CH3:29])=[C:19]([OH:21])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 1777704HCID 1777704, compound

Product 1

HCID 71278620HCID 71278620, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of (Z)-2-[(1H-indol-3-yl)methylene]-6-hydroxybenzofuran-3(2H)-one (0.030 g, 0.11 mmol) obtained in Example A1, Step 1 in ethanol (2.0 mL) was added with N,N,N′-trimethylpropane-1,3-diamine (0.015 g, 0.13 mmol), and 37% aqueous formaldehyde (0.011 g, 0.13 mmol), and the mixture was stirred overnight at 80° C. in a sealed tube. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10)) to obtain (Z)-2-[(1H-indol-3-yl)methylene]-7-({[3-(dimethylamino)propyl](methyl)amino}methyl)-6-hydroxybenzofuran-3(2H)-one (0.024 g, 54%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washthe residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10))

Sources & evidence

ORD record
ord-6ddb9d7f13a649c6a0dcb173d023a047
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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