Hydrazine → 1-(3-Benzylquinolin-2-yl)-2-methylpropan-1-amine

HRID 271825Notes

Reaction equation

HRID 271825 reaction equation
[CH2:1]([C:8]1[C:9]([CH:18]([N:22]2C(=O)C3C(=CC=CC=3)C2=O)[CH:19]([CH3:21])[CH3:20])=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN>C(O)C>[CH2:1]([C:8]1[C:9]([CH:18]([NH2:22])[CH:19]([CH3:20])[CH3:21])=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 9321Hydrazine2×HCID 598361922-[1-(3-benzylquinolin-2-yl)-2-methylpropyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 598361941-(3-Benzylquinolin-2-yl)-2-methylpropan-1-amineYield 49.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(3-benzylquinolin-2-yl)-2-methylpropan-1-amine 14 (91 mg, 1 eq.) in ethanol (2 ml), was added hydrazine (10 μl, 1.5 eq). The reaction was stirred at room temperature for an hour but very little product was detected. It was heated to 40° C. for 3 h and the 27% starting material was detected. More hydrazine (10 μl, 1.5 eq) was added and the reaction mixture was stirred for another half hour. The precipitate was filtered through a PTFE filter and washed with more CH2Cl2. The filtrate was concentrated and the crude product was purified by flash chromatography to yield 31 mg of 1-(3-benzylquinolin-2-yl)-2-methylpropan-1-amine 15 as clear oil.

Workup

  1. temperatureIt was heated to 40° C. for 3 h
  2. stirringthe reaction mixture was stirred for another half hour
  3. filtrationThe precipitate was filtered through a PTFE
  4. filtrationfilter
  5. washwashed with more CH2Cl2
  6. concentrationThe filtrate was concentrated
  7. customthe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-1ccb259b663744748296a19b0b5c74bb
Source dataset
uspto-grants-2008_11
Patent number
US07452996B2

Reaction notes

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