Ethanolamine → HCID 20038767, compound

HRID 1904275Notes

Reaction equation

HRID 1904275 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]([CH2:17][NH2:18])[OH:16]>C1(C)C(C)=CC=CC=1>[OH:16][CH2:15][CH2:17][NH:18][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

Participants

4

Reactant 2

HCID 700EthanolamineHCID 20038769HCID 20038769, compound

Product 1

HCID 20038767HCID 20038767, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

9-Chloro-5,6,7,8-tetrahydro-1H-pyrazolo[4,3-b]quinoline (2.45 g, 0.012 mole) and ethanolamine (2.2 ml, 0.036 mole) were heated under reflux in dry xylene (25 ml) for 24 hours. The solvent was evaporated off and the residue dissolved in water/methanol. The pH of the solution was adjusted to 9 by the addition of 10% sodium carbonate solution. The precipitate which formed was filtered off, washed with water, dried and recrystallised from ethyl acetate to give the title compound as a beige solid (0.55 g, 20%), m.p. 205°-210° C. Found: C, 62.05; H, 6.95; N, 24.00% C12H16N4O requires C, 62.05; H, 6.95; N, 24.10%

Workup

  1. customThe solvent was evaporated off
  2. dissolutionthe residue dissolved in water/methanol
  3. additionThe pH of the solution was adjusted to 9 by the addition of 10% sodium carbonate solution
  4. customThe precipitate which formed
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried
  8. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-cd9da3c0dbd34e93bef65a0a63f8438f
Source dataset
uspto-grants-1989_06
Patent number
US04837238

Reaction notes

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