Hydrazine → HCID 67543158, compound

HRID 389069Notes

Reaction equation

HRID 389069 reaction equation
NN.[S:3]1[C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:5]=[C:4]1[CH2:16][O:17][N:18]1C(=O)C2C(=CC=CC=2)C1=O>C(O)C>[NH2:18][O:17][CH2:16][C:4]1[S:3][C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:5]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 67542050HCID 67542050, compound

Product 1

HCID 67543158HCID 67543158, compoundYield 131.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine (3.4 g, 3.3 mL, 106 mmol) was added to a suspension of 2-[([1,3]thiazolo[4,5-c]quinolin-2-yl)methoxy]-1H-isoindole-1,3(2H)-dione (19.2 g, 53.1 mmol) in ethanol (300 mL), and the reaction was stirred at room temperature for 2.5 hours and filtered. The filter cake was washed with ethanol and dried overnight in a vacuum oven to provide 16.2 g of 2-(aminooxy)methyl[1,3]thiazolo[4,5-c]quinoline as a tan solid containing some phthalhydrazide. The filtrate was concentrated under reduced pressure to provide 5.89 g of the same mixture as a yellow solid. Some of the phthalhydrazide was removed from the mixture by recrystallization from ethanol.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with ethanol
  3. customdried overnight in a vacuum oven

Sources & evidence

ORD record
ord-d4418c10976a464886b2fea2b47b80dd
Source dataset
uspto-grants-2013_02
Patent number
US08378102B2

Reaction notes

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