Ethanol → HCID 70106633, compound

HRID 612483Notes

Reaction equation

HRID 612483 reaction equation
[CH2:1]([O:8][C:9]1[C:10](OC)=[C:11]([CH:16]=[CH:17]OC)[C:12]([Br:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:22].[NH:23]([C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1)[NH2:24].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:42]([OH:44])C>>[ClH:22].[CH2:1]([O:8][C:9]1[C:14]([O:44][CH3:42])=[CH:13][C:12]([Br:15])=[C:11]([CH2:16][CH:17]=[N:24][NH:23][C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 223202584-Hydrazinylpyridine hydrochlorideHCID 54239204HCID 54239204, compound

Product 1

HCID 70106633HCID 70106633, compoundYield 72.2%

Procedure

A mixture of 5-benzyloxy-2-bromo-4-methoxy-3-(2-methoxyvinyl)benzene (42.1 g), 4-hydrazinopyridine hydrochloride (19.0 g), p-toluenesulfonic acid (0.23 g) and ethanol (350 ml) was heated under reflux overnight, with stirring. The reaction mixture was cooled and filtered. Recrystallization of the precipitate from methanol yielded 40.2 g, (72.2%) of product, mp 232-233° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customRecrystallization of the precipitate from methanol

Sources & evidence

ORD record
ord-df82681ab1774668a1d4365f6d5b543f
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Reaction notes

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