Hydrazine → HCID 68539374, compound

HRID 1992619Notes

Reaction equation

HRID 1992619 reaction equation
NN.[NH2:3][C:4]1[C:13]2[N:14]=[CH:15][N:16]([CH2:17][CH2:18][CH2:19][CH2:20][O:21][N:22]3C(=O)C4C(=CC=CC=4)C3=O)[C:12]=2[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=1>C(O)C>[NH2:22][O:21][CH2:20][CH2:19][CH2:18][CH2:17][N:16]1[C:12]2[C:11]3[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=3[N:5]=[C:4]([NH2:3])[C:13]=2[N:14]=[CH:15]1

Participants

4

Reactant 2

HCID 9321Hydrazine2×HCID 68539763HCID 68539763, compound

Product 1

HCID 68539374HCID 68539374, compoundYield 135%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Anhydrous hydrazine (94 mg, 2.96 mmol) was added to 2-[4-(4-amino-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butoxy]-1H-isoindole-1,3(2H)-dione (600 mg, 1.48 mmol) in ethanol (25 mL) at ambient temperature. The reaction was stirred overnight, and additional hydrazine (2 equivalents) was added. After stirring for 2 hours at ambient temperature, the reaction was concentrated under reduced pressure. The residue was diluted with dichloromethane and concentrated under reduced pressure three times to remove the hydrazine and then dried under vacuum to provide 550 mg of impure 1-[4-(aminooxy)butyl]-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine as an orange solid.

Workup

  1. stirringAfter stirring for 2 hours at ambient temperature
  2. concentrationthe reaction was concentrated under reduced pressure
  3. additionThe residue was diluted with dichloromethane
  4. concentrationconcentrated under reduced pressure three times
  5. customto remove the hydrazine
  6. customdried under vacuum

Sources & evidence

ORD record
ord-6089199b34b24d29a8c553382a019f96
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

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