Water → HCID 24777314, compound

HRID 1817826Notes

Reaction equation

HRID 1817826 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.[CH:17]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18]1.C(N(CC)CC)C.O>C(O)C>[CH:17]1([NH:22][C:2]2[C:11]([C:12]#[N:13])=[CH:10][C:9]3[C:8](=[O:14])[CH2:7][C:6]([CH3:16])([CH3:15])[CH2:5][C:4]=3[N:3]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 2906CyclopentylamineHCID 8471TriethylamineHCID 13133972HCID 13133972, compound

Product 1

HCID 24777314HCID 24777314, 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 (0.25 g, 1.06 mmol), cyclopentylamine (0.136 g, 1.6 mmol) and triethylamine (0.154 ml, 0.11 g, 1.1 mmol) in ethyl alcohol (3 ml) was heated at reflux for 3 h. Then water (10 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) 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)

Sources & evidence

ORD record
ord-cf222ec9b7cb4c7187a271f4ae355e3d
Source dataset
uspto-grants-2009_10
Patent number
US07598384B2

Reaction notes

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