Water → 2-Cyclohexylamino-5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitrile

HRID 1817827Notes

Reaction equation

HRID 1817827 reaction equation
Cl[C:2]1[C:11]([C:12]#[N:13])=[CH:10][C:9]2[C:8](=[O:14])[CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.[CH:15]1([NH2:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(CC)CC)C.O>C(O)C>[CH:15]1([NH:21][C:2]2[C:11]([C:12]#[N:13])=[CH:10][C:9]3[C:8](=[O:14])[CH2:7][CH2:6][CH2:5][C:4]=3[N:3]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 7965CyclohexylamineHCID 8471TriethylamineHCID 247779422-Chloro-5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitrile

Product 1

HCID 247775802-Cyclohexylamino-5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitrileYield 59.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-chloro-5-oxo-5,6,7,8-tetrahydro-quinoline-3-carbonitrile (0.154 g, 0.75 mmol), cyclohexylamine (0.15 g, 1.5 mmol) and triethylamine (0.115 ml, 0.083 g, 0.82 mmol) in ethyl alcohol (3 ml) was heated at reflux for 3 h. Then water (10 ml) was added and the precipitated solid was filtered off and recrystallized from ethyl alcohol to give the title compound (0.12 g, 59%).

Workup

  1. temperatureat reflux for 3 h
  2. filtrationthe precipitated solid was filtered off
  3. customrecrystallized from ethyl alcohol

Sources & evidence

ORD record
ord-3c9b6c14b3da4889bb5f6da898750220
Source dataset
uspto-grants-2009_10
Patent number
US07598384B2

Reaction notes

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