p-Toluenesulfonic acid → HCID 70103652, compound

HRID 612467Notes

Reaction equation

HRID 612467 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]=[CH:11]OC.[NH:14]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[NH2:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][CH:11]=[N:15][NH:14][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 4166314-HydrazinopyridineHCID 53915085HCID 53915085, compound

Product 1

HCID 70103652HCID 70103652, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-bromo-1-methoxy-3-(2-methoxyvinyl)benzene (42.3 g), 4-hydrazinopyridine (27.6 g), and p-toluenesulfonic acid (3.3 g) in ethanol (500 ml) was heated under reflux overnight, with stirring. The reaction mixture was filtered, and the filtrate was concentrated to about 50% of its initial volume. The precipitate was collected to give 5.5 g of product, as the hydrochloride salt, and the filtrate was concentrated. Saturated sodium hydrogen carbonate solution was added to the residue and the mixture was extracted with ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was chromatographed on a Waters LC2000 instrument, gradient eluting with: 1% ethylamine/2% methanol/97% ethyl acetate/1% triethylamine acid/5% methanol/94% ethyl acetate. The appropriate fractions were collected and concentrated to yield 4.9 g (8.8%) of product, mp 142° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated to about 50% of its initial volume
  5. customThe precipitate was collected

Sources & evidence

ORD record
ord-2dc86b97a33f409b82a0eae7d3719f46
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Reaction notes

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