Ethanol → HCID 23153827, compound

HRID 1175795Notes

Reaction equation

HRID 1175795 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4](=[O:19])[C:3]=1[C:20]#[N:21].[OH:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][NH2:32])=[CH:27][CH:26]=1.C(N(CC)CC)C.[CH2:40]([OH:42])C>>[NH2:21][C:20]1[N:31]([C:28]2[CH:29]=[CH:30][C:25]([CH2:24][CH2:23][OH:22])=[CH:26][CH:27]=2)[N:32]=[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:42][CH3:40])=[CH:15][CH:14]=3)[C:4](=[O:19])[C:3]=12

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 578496HCID 578496, compoundHCID 23154051HCID 23154051, compound

Product 1

HCID 23153827HCID 23153827, compound

Procedure

A mixture of 4-chloro-1-benzyl-2-oxo-1,2-dihydroquinoline-3-carbonitrile (0.6 g), 4-(2-hydroxyethyl)phenylhydrazine (0.24 g), triethylamine (0.27 ml) and ethanol (40 ml) was heated under reflux for 12 hours. The solvent was distilled off under reduced pressure, and an aqueous sodium hydrogen carbonate solution was added thereto and extracted with ethyl acetate. The extract was washed with water and brine, dried and concentrated. The residue was purified with silica gel column chromatography to obtain the target compound (0.47 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionan aqueous sodium hydrogen carbonate solution was added
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water and brine
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-8b5f13a722ee45c58f9b758c662a4c42
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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