Water → HCID 24777313, compound

HRID 1817829Notes

Reaction equation

HRID 1817829 reaction equation
Cl[C:2]1[C:11]([C:12]#[N:13])=[CH:10][C:9]2[C:8](=[O:14])[CH2:7][C:6]([CH3:16])([CH3:15])[CH2:5][C:4]=2[N:3]=1.[CH2:17]([NH:24][CH3:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.O>C(O)C>[CH2:17]([N:24]([CH3:25])[C:2]1[C:11]([C:12]#[N:13])=[CH:10][C:9]2[C:8](=[O:14])[CH2:7][C:6]([CH3:16])([CH3:15])[CH2:5][C:4]=2[N:3]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7669N-MethylbenzylamineHCID 8471TriethylamineHCID 13133972HCID 13133972, compound

Product 1

HCID 24777313HCID 24777313, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-chloro-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-quinoline-3-carbonitrile (0.22 g, 0.94 mmol), benzyl(methyl)amine (0.17 g, 1.4 mmol) and triethylamine (0.14 ml, 0.1 g, 1.0 mmol) in ethyl alcohol (3 ml) was heated at reflux for 3 h. Then water (20 ml) was added and the mixture was extracted by dichloromethane. The extract was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel (CH2Cl2-hexane, 1:1). The product obtained was recrystallized from ethyl alcohol to give the title compound (0.145 g, 48%).

Workup

  1. temperatureat reflux for 3 h
  2. extractionthe mixture was extracted by dichloromethane
  3. concentrationThe extract was concentrated under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (CH2Cl2-hexane, 1:1)
  5. customThe product obtained
  6. customwas recrystallized from ethyl alcohol

Sources & evidence

ORD record
ord-1170bbb63bd64c3a81c0634f0b1d4595
Source dataset
uspto-grants-2009_10
Patent number
US07598384B2

Reaction notes

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