Hydrazine hydrate (1:1) → O-{[4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl}hydroxylamine

HRID 599394Notes

Reaction equation

HRID 599394 reaction equation
O.NN.[NH2:4][C:5]1[C:14]2[N:15]=[C:16]([CH2:22][O:23][N:24]3C(=O)C4C(=CC=CC=4)C3=O)[N:17]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:13]=2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]=1>C(O)C>[NH2:4][C:5]1[C:14]2[N:15]=[C:16]([CH2:22][O:23][NH2:24])[N:17]([CH2:18][CH:19]([CH3:20])[CH3:21])[C:13]=2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67052437HCID 67052437, compound

Product 1

HCID 11414929O-{[4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl}hydroxylamineYield 77.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (9 mL) was added to a suspension of 2-{[4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methoxy}isoindole-1,3-dione (3.9 g) in ethanol (90 mL). The resulting solution was stirred at ambient temperature for 3 hours. The reaction mixture was filtered to remove a precipitate and the filter cake was washed with ethanol and dichloromethane. The filtrate was concentrated under reduced pressure, diluted with aqueous 1N hydrochloric acid (100 mL), and then washed sequentially with dichloromethane (2×50 mL) and ethyl acetate (1×50 mL). Analysis of the organic washes by LCMS indicated that they did not contain product. The aqueous acidic layer was made basic (˜pH 9) with solid sodium carbonate and then extracted sequentially with dichloromethane (1×100 mL), ethyl acetate (1×100 mL), and dichloromethane (1×100 mL). The combined organic extracts were dried over magnesium sulfate, filtered and then concentrated under reduced pressure to provide 2.07 g of O-{[4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl}hydroxylamine as a tan foam.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove a precipitate
  3. washthe filter cake was washed with ethanol and dichloromethane
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additiondiluted with aqueous 1N hydrochloric acid (100 mL)
  6. washwashed sequentially with dichloromethane (2×50 mL) and ethyl acetate (1×50 mL)
  7. extractionextracted sequentially with dichloromethane (1×100 mL), ethyl acetate (1×100 mL), and dichloromethane (1×100 mL)
  8. dry with materialThe combined organic extracts were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-42a057faa4c145a4bfc4cacecb2da938
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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