Triethylamine → 9-amino-1-methyl-5,6-dihydro-1H-[1,2,4]triazino[4,3-a]quinolin-2(3H)-one

HRID 519080Notes

Reaction equation

HRID 519080 reaction equation
CC1[N:3]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][C:14]4[N:15]3[CH:18]([CH3:23])[C:19](=[O:22])[NH:20][N:21]=4)=[CH:10][CH:9]=2)C(C)=CC=1.C(N(CC)CC)C.Cl.NO>CCO.O>[NH2:3][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][C:14]3[N:15]2[CH:18]([CH3:23])[C:19](=[O:22])[NH:20][N:21]=3)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 867274469-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-5,6-dihydro-1H-[1,2,4]triazino[4,3-a]quinolin-2(3H)-one

Product 1

HCID 867274479-amino-1-methyl-5,6-dihydro-1H-[1,2,4]triazino[4,3-a]quinolin-2(3H)-oneYield 67.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 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 (0.140 g, 0.45 mmol) and triethylamine (0.138 g, 1.362 mmol) in EtOH (9 mL) was added a solution of hydroxylamine hydrochloride (0.095 g, 1.362 mmol) in water (3 mL) and the reaction mixture was heated to reflux for 3 h. The reaction mixture was cooled to ambient temperature and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel (eluting with 50-100% EtOAc in petroleum ether) to give 9-amino-1-methyl-5,6-dihydro-1H-[1,2,4]-triazino[4,3-a]quinolin-2(3H)-one (0.070 g, 67%). 1H NMR (CDCl3, 400 MHz): δ 8.06 (brs, 1H), 6.91 (d, J=8.0 Hz, 1H), 6.31 (d, J=8.0 HZ, 1H), 6.26 (s, 1H), 4.60 (q, J=6.8 HZ, 1H), 3.63 (brs, 2H), 2.67 (m, 2H), 2.53 (m, 2H), 1.42 (d, J=6.8 Hz, 3H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 3 h
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified by column chromatography on silica gel (eluting with 50-100% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-70bd586d8041416286a6ea3601006e14
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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