4-(Dimethylamino)Benzaldehyde → HCID 70455102, compound

HRID 365125Notes

Reaction equation

HRID 365125 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].[CH2:8]([Br:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:16][N:17]([CH3:26])[C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.N1CCCCC1>C(O)(C)C.CO>[Br-:15].[CH2:8]([N+:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[CH:22][C:21]1[CH:24]=[CH:25][C:18]([N:17]([CH3:26])[CH3:16])=[CH:19][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 74794-(Dimethylamino)BenzaldehydeHCID 7498Benzyl BromideHCID 79752-MethylpyridineHCID 8082Piperidine

Product 1

HCID 70455102HCID 70455102, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

2-Picoline (9.3 g, 0.1 mole) and benzyl bromide (17.1 g, 0.1 mole) were refluxed in isopropanol (50 ml) overnight. The solvent was evaporated giving an oil which was heated at 100° C. for six hours. The resulting crude oil (8.0 g, 0.03 mole) and 4-dimethylaminobenzaldehyde (4.6 g, 0.03 mole) were refluxed in methanol (50 ml) in the presence of piperidine (0.2 ml) under nitrogen for three hours. On cooling dark-coloured crystals were obtained which were collected to give 1-benzyl-2-[4-(dimethylamino)styryl]pyridinium bromide (6.8 g), melting point 250°-251° C.

Workup

  1. customThe solvent was evaporated
  2. customgiving an oil which
  3. temperatureOn cooling dark-coloured crystals
  4. customwere obtained which
  5. customwere collected

Sources & evidence

ORD record
ord-b82745c0cfca440aaa240c10344dad7a
Source dataset
uspto-grants-1986_08
Patent number
US04608379

Reaction notes

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