Hydrazine → HCID 68539374, compound

HRID 1187425Notes

Reaction equation

HRID 1187425 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 sting 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]quinolin4-amine as an orange solid.

Workup

  1. waitAfter sting 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-d8aab179250049069e08957606f36398
Source dataset
uspto-grants-2014_03
Patent number
US08673932B2

Reaction notes

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