Hydrazine hydrate (1:1) → 9-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-5,6-dihydro-1H-[1,2,4]triazino[4,3-a]quinolin-2(3H)-one

HRID 519079Notes

Reaction equation

HRID 519079 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][C:14](=S)[N:15]3[CH:18]([CH3:24])[C:19](OCC)=[O:20])=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.O.[NH2:27][NH2:28]>CCO>[CH3:7][C:4]1[N:3]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][C:14]4[N:15]3[CH:18]([CH3:24])[C:19](=[O:20])[NH:27][N:28]=4)=[CH:10][CH:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86727445ethyl 2-(7-(2,5-dimethyl-1H-pyrrol-1-yl)-2-thioxo-3,4-dihydroquinolin-1(2H)-yl)propanoate

Product 1

HCID 867274469-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-5,6-dihydro-1H-[1,2,4]triazino[4,3-a]quinolin-2(3H)-oneYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(7-(2,5-dimethyl-1H-pyrrol-1-yl)-2-thioxo-3,4-dihydroquinolin-1(2H)-yl)propanoate (0.2 g, 0.561 mmol) in EtOH (10 mL) was added hydrazine hydrate (6 mL) and the solution was heated to reflux overnight. The reaction mixture was cooled to ambient temperature and the solvent was removed in vacuo. Water (10 mL) was added to the residue and the mixture was extracted with EtOAc (2×30 mL). The combined organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 30-50% EtOAc in petroleum ether) to give 9-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-5,6-dihydro-1H-[1,2,4]-triazino[4,3-a]quinolin-2(3H)-one (0.14 g, 81%). 1H NMR (CDCl3, 400 MHz): δ 8.04 (brs, 1H), 7.21 (d, J=8.0 Hz, 1H), 6.82 (d, J=8.0 Hz, 1H), 6.73 (s, 1H), 5.89 (s, 2H), 4.56 (q, J=6.8 Hz, 1H), 2.93 (m, 2H), 2.63 (m, 2H), 2.05 (s, 6H), 1.42 (d, J=6.8 Hz, 3H).

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux overnight
  3. customthe solvent was removed in vacuo
  4. additionWater (10 mL) was added to the residue
  5. extractionthe mixture was extracted with EtOAc (2×30 mL)
  6. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography on silica gel (eluting with 30-50% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-7b00a39fc7bb4625bbc344f03a7f0a57
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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