Hydrochloric Acid → 3-Quinolinecarbonitrile, 4-hydroxy-

HRID 612003Notes

Reaction equation

HRID 612003 reaction equation
CN([CH:4]=[N:5][C:6]1[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10]C)=O)C.C[O-].[Na+].[C:19](#[N:21])[CH3:20].Cl>O.C1(C)C=CC=CC=1>[O:10]=[C:8]1[C:7]2[C:6](=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:5][CH:4]=[C:20]1[C:19]#[N:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 10942334Sodium MethoxideHCID 13058944HCID 13058944, compound

Product 1

HCID 35393493-Quinolinecarbonitrile, 4-hydroxy-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A stirred mixture of 1.03 g of methyl 2-(dimethylaminomethyleneamino)benzoate, 0.54 g of sodium methoxide, 1.04 ml of acetonitrile, and 10 ml of toluene was refluxed for 18 h. The mixture was cooled, treated with water, and brought to pH 3 by addition of dilute HCl. The resulting solid was extracted with ethyl acetate. The extract was washed with water, dried and evaporated. The residue was recrystallized from ethanol to give a solid, mp 290-300° C.

Workup

  1. temperaturewas refluxed for 18 h
  2. temperatureThe mixture was cooled
  3. extractionThe resulting solid was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customevaporated
  7. customThe residue was recrystallized from ethanol
  8. customto give a solid, mp 290-300° C.

Sources & evidence

ORD record
ord-27e5f83834ba43c1bf159db5906dea3a
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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