Hydrazine hydrate (1:1) → HCID 136374695, compound

HRID 1467694Notes

Reaction equation

HRID 1467694 reaction equation
O[C:2]1[C:11]2[C:10]([C:12](OCC)=[O:13])=[CH:9][CH:8]=[CH:7][C:6]=2[NH:5][C:4](=[O:17])[C:3]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O.[NH2:25][NH2:26]>CO>[C:18]1([CH:3]2[C:2]3=[N:25][NH:26][C:12](=[O:13])[C:10]4[CH:9]=[CH:8][CH:7]=[C:6]([C:11]=43)[NH:5][C:4]2=[O:17])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67259322HCID 67259322, compound

Product 1

HCID 136374695HCID 136374695, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

Ethyl 4-hydroxy-2-oxo-3-phenyl-1,2-dihydroquinoline-5-carboxylate (330 mg, 1.1 mmol) was added to hydrazine monohydrate (1 mL) and methanol (2 mL), the mixture was stirred at 110° C. for 2.5 h by microwave. Then the mixture was cooled to room temperature, the solvent was evaporated in vacuum. The residue was washed with methanol, and then purified by column chromatography (silica gel, dichloromethane/methanol=300:1 to 50:1) to obtain a pale white solid (148 mg, yield 53%). LC-MS (ESI) m/z: 278 (M+1)+. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 5.09 (s, 1H), 7.17-7.40 (m, 6H), 7.77-7.81 (m, 2H), 11.10 (s, 1H), 12.57 (s, 1H).

Workup

  1. temperatureThen the mixture was cooled to room temperature
  2. customthe solvent was evaporated in vacuum
  3. washThe residue was washed with methanol
  4. custompurified by column chromatography (silica gel, dichloromethane/methanol=300:1 to 50:1)

Sources & evidence

ORD record
ord-860085f84c684b7cac287e6035eaee93
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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