N-methyl-N-phenyl-hydrazine → 4-(diethylamino)salicylaldehyde N-methyl-N-phenylhydrazone

HRID 349143

Reaction equation

HRID 349143 reaction equation
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]1[CH:5]=[C:6]([OH:12])[C:7](=[CH:10][CH:11]=1)[CH:8]=O)[CH3:2].[CH3:15][N:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH2:17]>CC(O)C>[CH3:15][N:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[N:17]=[CH:8][C:7]1[C:6](=[CH:5][C:4]([N:3]([CH2:13][CH3:14])[CH2:1][CH3:2])=[CH:11][CH:10]=1)[OH:12]

Participants

4

Reactant 2

HCID 36299N-methyl-N-phenyl-hydrazineHCID 872934-(Diethylamino)-2-hydroxybenzaldehyde2×

Product 1

HCID 1363784264-(diethylamino)salicylaldehyde N-methyl-N-phenylhydrazoneYield 84%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-(diethylamino)salicylaldehyde (10 g, 52 mmol, obtained from Aldrich) dissolved in 80 ml of 2-propanol, and N-methyl-N-phenylhydrazine (6.8 ml, 63 mmol, obtained from Aldrich) was added to a 250 ml round bottom flask equipped with a reflux condenser and a magnetic stirrer. The reaction mixture was refluxed until 4-(diethylamino)salicylaldehyde completely reacted. After the termination of the reaction, the reaction mixture was cooled to room temperature. The crystals formed were filtered and washed repeatedly with cold 2-propanol and dried under vacuum to yield 12.9 g (84%) of 4-(diethylamino)salicylaldehyde N-methyl-N-phenylhydrazone. The melting point was found to be 75.5–76.5° C. (recrystallized from 2-propanol). The 1H-NMR spectrum (100 Mhz) of the product in CDCl3 was characterized by the following chemical shifts (in ppm): 11.53 (s, 1H, OH); 7.63 (s, 1H, N═CH); 7.50–6.80 (m, 6H, Ar); 6.26 (m, 2H, Ar); 3.37 (m, 7H, CH2CH3, NCH3); 1.18 (t, 6H, CH2CH3, J=7.0 Hz). An elemental analysis yielded the following results in weight percent: C, 72.61; H, 7.88; N, 14.20, which compared with calculated values for C18H23N3O in weight percent of: C, 72.70; H, 7.80; N, 14.13.

Workup

  1. customequipped with a reflux condenser and a magnetic stirrer
  2. customcompletely reacted
  3. customAfter the termination of the reaction
  4. customThe crystals formed
  5. filtrationwere filtered
  6. washwashed repeatedly with cold 2-propanol
  7. customdried under vacuum

Sources & evidence

ORD record
ord-badb4a44c132472e8a3936e464b862e9
Source dataset
uspto-grants-2007_02
Patent number
US07179574B2

Linked notes

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