Hydrazine → (6-Bromoquinolin-2-YL)methanamine

HRID 2075679Notes

Reaction equation

HRID 2075679 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12]Cl)[CH:6]=[CH:5]2.C[N:15](C=O)C.CC#N.C1(=O)NC(=O)C2=CC=CC=C12.[K].NN>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][NH2:15])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 9321HydrazineHCID 21891449acetonitrile N,N-dimethylformamideHCID 24194345Phthalimide potassium saltHCID 582577966-Bromo-2-(chloromethyl)quinoline

Product 1

HCID 57365264(6-Bromoquinolin-2-YL)methanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To 4a (440 mg, 1.7 mmol) in 1:1 DMF/MeCN (3 mL) at room temperature was added potassium phthalimide (350 mg, 1.9 mmol), and the reaction was heated to 60° C. overnight. The mixture was poured into water and filtered, and the solid was suspended in EtOH (10 mL). Hydrazine (82 mg, 2.5 mmol) was added, and the mixture was heated to 70° C. for 30 minutes. The reaction was then concentrated, and the crude material, 4b, was used directly in the next step.

Workup

  1. filtrationfiltered
  2. temperaturethe mixture was heated to 70° C. for 30 minutes
  3. concentrationThe reaction was then concentrated

Sources & evidence

ORD record
ord-7e64c20909c147378045c443b04ce6d6
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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