Citric Acid → HCID 135599916, compound

HRID 1175804Notes

Reaction equation

HRID 1175804 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[NH:5][C:4](=[O:16])[C:3]=1[C:17]#[N:18].Cl.[CH2:20]([O:27][C:28]1[CH:29]=[CH:30][C:31]([CH3:36])=[C:32]([NH:34][NH2:35])[CH:33]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[NH2:18][C:17]1[N:34]([C:32]2[CH:33]=[C:28]([O:27][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:29]=[CH:30][C:31]=2[CH3:36])[N:35]=[C:2]2[C:11]3[CH:10]=[C:9]([O:12][CH3:13])[C:8]([O:14][CH3:15])=[CH:7][C:6]=3[NH:5][C:4](=[O:16])[C:3]=12

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 23153983HCID 23153983, compoundHCID 23154019HCID 23154019, compound

Product 1

HCID 135599916HCID 135599916, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-chloro-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile (53 mg), 5-benzyloxy-2-methylphenylhydrazine hydrochloride (53 mg), triethylamine (84 μl) and ethanol (5 ml) was stirred at 80° C. for 24 hours. After cooling, 10% citric acid was added thereto, extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography to obtain the target compound (68 mg).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-d2fe5513bb78464a93a66291b8b8cdd6
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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