Hydrochloric Acid → HCID 326819, compound

HRID 1920685Notes

Reaction equation

HRID 1920685 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.Cl.[CH:12](=O)/[CH:13]=[CH:14]/[CH3:15].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]2[C:6]([CH:12]=[CH:13][C:14]([CH3:15])=[N:9]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 76084N,N-dimethyl-m-phenylenediamineHCID 447466Crotonaldehyde

Product 1

HCID 326819HCID 326819, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Referring to FIG. 21, a mixture of N,N-dimethyl-meta-phenylene-diamine (800 mg, 3.8 mmol) and 6 N HCl (12 mL) was stirred at reflux. Crotonaldehyde (0.31 mL, 3.8 mmol) dissolved in toluene (1 mL) was added dropwise to the purple solution. The reaction mixture was stirred for 2 h, cooled and neutralized with solid NaOH, and extracted with toluene, then chloroform (×5). The extracts were combined, dried over Na2SO4 and evaporated to dryness. The residue was purified by column chromatography (EtOAc) to obtain 13a (304.3 mg, 1.6 mmol, 43% yield): 1H NMR (CDCl3) δ 7.84 (1H, d, J=8.4 Hz), 7.58 (1H, d, J=8.8 Hz), 7.09 (2H, m), 6.98 (1H, d, J=8. Hz), 3.06 (6H, s), 2.66 (3H, s); 13C NMR (CDCl3) δ 159.3, 151.5, 149.9, 135.8, 128.6, 119.2, 118.2, 115.5, 106.8, 40.8, 25.6; FTIR (neat) 2918, 2804, 1620, 1600, 1514, 1379, 1155, 1062, 827 cm−1.

Workup

  1. temperatureat reflux
  2. additionwas added dropwise to the purple solution
  3. stirringThe reaction mixture was stirred for 2 h
  4. extractionextracted with toluene
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness
  7. customThe residue was purified by column chromatography (EtOAc)

Sources & evidence

ORD record
ord-4f4482033da5490fa2445b8715d7c001
Source dataset
uspto-grants-2012_05
Patent number
US08173620B2

Reaction notes

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