Hydrazine → HCID 59497153, compound

HRID 389062Notes

Reaction equation

HRID 389062 reaction equation
NN.[NH2:3][C:4]1[C:13]2[N:14]=[C:15]([CH2:17][O:18][N:19]3C(=O)C4C(=CC=CC=4)C3=O)[S:16][C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=1>C(O)C>[NH2:19][O:18][CH2:17][C:15]1[S:16][C:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]=[C:4]([NH2:3])[C:13]=2[N:14]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 59497152HCID 59497152, compound

Product 1

HCID 59497153HCID 59497153, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine (2.25 mL, 71.7 mmol) was added to a suspension of 2-[(4-amino[1,3]thiazolo[4,5-c]quinolin-2-yl)methoxy]-1H-isoindole-1,3(2H)-dione (5.4 g, 14 mmol) in ethanol (200 mL), and the reaction was heated at reflux for one hour and filtered hot to remove a solid. The filtrate was concentrated under reduced pressure and further dried in a vacuum oven overnight The resulting solid (4.89 g) was triturated with ethanol (200 mL) for two hours, filtered, washed with ethanol, and dried in a vacuum oven to provide 3.05 g of 2-(aminooxy)methyl[1,3]thiazolo[4,5-c]quinolin-4-amine as an orange solid containing some phthalhydrazide. The filtrate was concentrated under reduced pressure to provide an additional 1.91 g of the product mixture.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for one hour
  3. filtrationfiltered hot
  4. customto remove a solid
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. dry with materialfurther dried in a vacuum oven overnight The resulting solid (4.89 g)
  7. customwas triturated with ethanol (200 mL) for two hours
  8. filtrationfiltered
  9. washwashed with ethanol
  10. customdried in a vacuum oven

Sources & evidence

ORD record
ord-d1bf4e37122f41708e9c3a94139c1d9d
Source dataset
uspto-grants-2013_02
Patent number
US08378102B2

Reaction notes

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