Potassium Carbonate → HCID 22466732, compound

HRID 1934979Notes

Reaction equation

HRID 1934979 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:17][CH2:18][CH2:19][O:20][CH3:21])[C:10]=2[O:12][CH2:13][CH2:14][O:15][CH3:16])[N:5]=[CH:4][C:3]=1[C:22]#[N:23].Cl.N1C=CC=CC=1.[C:31]([C:33]1[CH:34]=[C:35]([CH:37]=[CH:38][CH:39]=1)[NH2:36])#[CH:32].C(OC(O)C)C.C(=O)([O-])[O-].[K+].[K+]>O>[C:31]([C:33]1[CH:34]=[C:35]([NH:36][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:17][CH2:18][CH2:19][O:20][CH3:21])[C:10]=3[O:12][CH2:13][CH2:14][O:15][CH3:16])[N:5]=[CH:4][C:3]=2[C:22]#[N:23])[CH:37]=[CH:38][CH:39]=1)#[CH:32]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 104682Benzenamine, 3-ethynyl-HCID 101298981-EthoxyethanolHCID 10176127Pyridinium chlorideHCID 22466727HCID 22466727, compound

Product 1

HCID 22466732HCID 22466732, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 4-Chloro-5,6-bis(2-methoxyethoxy)-3-quinolinecarbonitrile (2.52 g, 7.5 mmol), pyridine hydrochloride (0.87 g, 9.0 mmol), 3-ethynylaniline (1.06 g, 9.0 mmol), and ethoxyethanol (22 ml) was refluxed for 1.5 h, cooled, diluted with water containing potassium carbonate to give pH˜9, and extracted with ethyl acetate. The extract was washed well with water, dried, and concentrated. The resulting solid was recrystallized from ethyl acetate to give an off-white solid, mp 150-153°.

Workup

  1. temperaturewas refluxed for 1.5 h
  2. temperaturecooled
  3. customto give pH˜9
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed well with water
  6. customdried
  7. concentrationconcentrated
  8. customThe resulting solid was recrystallized from ethyl acetate
  9. customto give an off-white solid, mp 150-153°

Sources & evidence

ORD record
ord-212cb200cc354268b154450b673e2bb8
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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