3,4-Dimethylaniline → HCID 53651546, compound

HRID 487657Notes

Reaction equation

HRID 487657 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([CH3:13])[CH:7]=1.C([O-])(=O)C.[Na+].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[CH2:24][CH:25](C(C)=O)[C:26]([O:28][CH3:29])=[O:27]>O.Cl>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH2:24][CH:25]([NH:1][NH:5][C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([CH3:13])[CH:7]=2)[C:26]([O:28][CH3:29])=[O:27])[CH:33]=[CH:34][C:35]=1[O:36][CH3:37]

Participants

7

Reactant 4

HCID 72483,4-DimethylanilineHCID 517045Sodium AcetateHCID 10611783HCID 10611783, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 53651546HCID 53651546, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of sodium nitrite (0.414 g) in water (2.0 ml) was dropwise added to a solution of 3,4-xylidine (0.61 g) in concentrated hydrochloric acid (1.5 ml) at a temperature of 0° C., followed by stirring for 30 minutes at 0° C. To the mixture were added sodium acetate (1.23 g) and methyl 2-(3,4-dimethoxybenzyl)acetoacetate (1.33 g). After stirring for an hour at room temperature, the reaction mixture was poured into water and extracted with ethyl ether. The ethereal layer was washed with a saturated sodium hydrogencarbonate aqueous solution and water, dried (MgSO4) and concentrated under reduced pressure. The residue was dissolved in methanol (20 ml), to which 1N-KOH methanolic solution (5 ml) was dropwise added at 0° C. After stirring for an hour at 0° C., the resultant mixture was neutralized with acetic acid and poured into water. The precipitate was collected by filtration and recrystallized from acetone-methanol to give methyl 3-(3,4-dimethoxyphenyl)-2-(3,4 -dimethylphenylhydrazino)propionate (1.25 g, 70%) as pale red prisms.

Workup

  1. stirringAfter stirring for an hour at room temperature
  2. extractionextracted with ethyl ether
  3. washThe ethereal layer was washed with a saturated sodium hydrogencarbonate aqueous solution and water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in methanol (20 ml), to which 1N-KOH methanolic solution (5 ml)
  7. additionwas dropwise added at 0° C
  8. stirringAfter stirring for an hour at 0° C.
  9. additionpoured into water
  10. filtrationThe precipitate was collected by filtration
  11. customrecrystallized from acetone-methanol

Sources & evidence

ORD record
ord-37a1ed42424d453d8e04651b14aadc7b
Source dataset
uspto-grants-1994_03
Patent number
US05296499

Reaction notes

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