4-(Ethyl(2-hydroxyethyl)amino)benzaldehyde → HCID 15219579, compound

HRID 1416339Notes

Reaction equation

HRID 1416339 reaction equation
[CH2:1]([N:3]([C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)[CH2:4][CH2:5][OH:6])[CH3:2].[I-:15].[CH3:16][C:17]1[CH:22]=[CH:21][N+:20]([CH2:23][CH2:24][OH:25])=[CH:19][CH:18]=1>C(O)C>[I-:15].[CH2:1]([N:3]([C:7]1[CH:14]=[CH:13][C:10](/[CH:11]=[CH:16]/[C:17]2[CH:22]=[CH:21][N+:20]([CH2:23][CH2:24][OH:25])=[CH:19][CH:18]=2)=[CH:9][CH:8]=1)[CH2:4][CH2:5][OH:6])[CH3:2]

Participants

4

Reactant 2

HCID 6398574-(Ethyl(2-hydroxyethyl)amino)benzaldehydeHCID 15219576HCID 15219576, compound

Product 1

HCID 15219579HCID 15219579, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the procedure of Example 6, equimolar amounts of 4-(N-ethyl-N-hydroxyethylamino)benzaldehyde, prepared according to Example 2, and 4-methyl-N-(2-hydroxyethyl)pyridinium iodide, prepared according to Example 4, were reacted in ethanol at reflux, overnight. Upon cooling, dye3 precipitated as a red solid and was collected by filtration, washed, and dried. Yield: 67%. 1H-NMR (DMSO)-d6): δ1.0 (t, 3H), 3.3 (q, 2H), 3.40 (q, 2H), 3.50 (t, 2H), 3.80 (q, 2H), 4.40 (t, 2H), 4.70 (t, 1H), 5.2 (t, 1H), 6.7 (d, 2H), 7.1 (d, 1H), 7.80 (d, 2H), 7.90 (d, 1H), 8.10 (d, 2H), 8.70 (d, 2H) ppm. The elements analy. calcd. for C19H25IN2O2 : C, 51.8; H, 5.7; N, 6.4; Found: C, 51.5; H, 5.7; N, 7.1. Td 270° C.

Workup

  1. customprepared
  2. customprepared
  3. temperatureat reflux, overnight
  4. temperatureUpon cooling
  5. customdye3 precipitated as a red solid
  6. filtrationwas collected by filtration
  7. washwashed
  8. customdried
  9. customTd 270° C.

Sources & evidence

ORD record
ord-0c19f4aa57814f3c90cdafa05e6b0a77
Source dataset
uspto-grants-1999_06
Patent number
US05912257

Reaction notes

Loading…