4-(Dimethylamino)-cinnamaldehyde → HCID 70896482, compound

HRID 1946213Notes

Reaction equation

HRID 1946213 reaction equation
[Cl-].[C:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH+:10]=[C:9]([CH3:14])[C:8]2([CH3:16])[CH3:15])([OH:4])=[O:3].[CH3:17][N:18]([CH3:29])[C:19]1[CH:28]=[CH:27][C:22]([CH:23]=[CH:24][CH:25]=O)=[CH:21][CH:20]=1>C(#N)C>[CH3:17][N:18]([CH3:29])[C:19]1[CH:28]=[CH:27][C:22]([C:23]2[CH:24]=[CH:25][N+:10]3[C:11]4[C:7]([C:8]([CH3:16])([CH3:15])[C:9]=3[CH:14]=2)=[CH:6][C:5]([C:2]([O-:4])=[O:3])=[CH:13][CH:12]=4)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 922244-(Dimethylamino)-cinnamaldehydeHCID 68725913HCID 68725913, compound

Product 1

HCID 70896482HCID 70896482, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 5-carboxy-2,3,3-trimethyl-3H-indolium chloride (14.5 g, 60.5 mmol) and 4-dimethylamino cinnamaldehyde (10.6 g, 60.5 mmol) in 200 ml of acetonitrile was heated to 60° C. for 24 h. The solvent was removed under vacuum and the resulting residue was subjected to silica gel chromatography twice. Then, recrystallization from methanol and ether afforded 10 g of target compound.

Workup

  1. customThe solvent was removed under vacuum
  2. customThen, recrystallization from methanol and ether
  3. customafforded 10 g of target compound

Sources & evidence

ORD record
ord-1b9c148db5c34c768aee339ec5bf170d
Source dataset
uspto-grants-2013_03
Patent number
US08398722B2

Reaction notes

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