Hydrochloric Acid → HCID 178492077, compound

HRID 1241892Notes

Reaction equation

HRID 1241892 reaction equation
O[C:2]1[C:3](=[O:23])[N:4]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH2:5][CH2:6][C:7]=1[C:8](=[O:13])C(F)(F)F.Cl.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][NH2:34])=[CH:29][CH:28]=1.C(N(CC)CC)C.Cl>C1COCC1>[OH:13][C:8]1[C:7]2[CH2:6][CH2:5][N:4]([C:14]3[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=3)[C:3](=[O:23])[C:2]=2[N:33]([C:30]2[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=2)[N:34]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 21936827HCID 21936827, compound

Product 1

HCID 178492077HCID 178492077, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Part C. A mixture of the 3-hydroxy-1-(4-nitrophenyl)-4-(trifluoroacetyl)-5,6-dihydro-2(1H)-pyridinone made above (4.91 g, 12.94 mmol), p-methoxyphenylhyrazine HCl salt (2.37 g, 13.59 mmol) in 100 mL of THF was treated with 3.62 mL of triethylamine at rt overnight. To the reaction mixture was added 100 mL of 1N HCl. The resulting mixture was refluxed for 2 h. After cool to rt the title compound was collect by filtration (4.5 g, 92%). 1H NMR (DMSO-d6, 300 MHz) δ 8.24 (2H, d, J=9.2 Hz), 7.64 (2H, d, J=9.0 Hz), 7.39 (2H, d, J=9.0 Hz), 6.94(2H, t, J=9.2 Hz), 4.13 (2H, t, J=6.6 Hz), 3.77 (3H, s), 2.85 (2H, t, J=6.6 Hz) ppm.

Workup

  1. temperatureThe resulting mixture was refluxed for 2 h

Sources & evidence

ORD record
ord-217d35fdee65455099f487c481d347e7
Source dataset
uspto-grants-2006_10
Patent number
US07115627B2

Reaction notes

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