Isobutylamine → HCID 20038756, compound

HRID 1904276Notes

Reaction equation

HRID 1904276 reaction equation
Cl[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=[C:4]2[CH:12]=[N:13][NH:14][C:3]=12.[CH2:15]([NH2:19])[CH:16]([CH3:18])[CH3:17]>C1(C)C(C)=CC=CC=1>[CH2:15]([NH:19][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=[C:4]2[CH:12]=[N:13][NH:14][C:3]=12)[CH:16]([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 20038769HCID 20038769, compound

Product 1

HCID 20038756HCID 20038756, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

9-Chloro-5,6,7,8-tetrahydro-1H-pyrazolo[4,3-b]quinoline (4.90 g, 0.024 mole) and isobutylamine (11.7 ml, 0.118 mole) were heated under reflux under nitrogen in dry xylene (50 ml) for 6 days. The solution was concentrated to dryness, the residue dissolved in water/methanol and the solution adjusted to pH 9-10 by addition of 10% sodium carbonate solution. The precipitate was filtered of, washed with water, dried and recrystallised from ethyl acetate to give the title compound as a beige solid (0.85 g, 15%), m.p. 124°-127° C. Found: C, 68.45; H, 8.55; N, 22.80%. C14H20N4 requires C, 68.80; H, 8.25; N, 22.95%.

Workup

  1. concentrationThe solution was concentrated to dryness
  2. dissolutionthe residue dissolved in water/methanol
  3. additionthe solution adjusted to pH 9-10 by addition of 10% sodium carbonate solution
  4. filtrationThe precipitate was filtered of,
  5. washwashed with water
  6. customdried
  7. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-02c539d0f8d347c2bfb685ddcc5f455e
Source dataset
uspto-grants-1989_06
Patent number
US04837238

Reaction notes

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