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Hydrochloric Acid → 3-Quinolinecarbonitrile, 4-hydroxy-

HRID 1934922
Notes
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Reaction equation

HRID 1934922 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 10942334Sodium MethoxideHCID 13058944Anthranilic acid, N-dimethylaminomethylene-, methyl ester

Product 1

HCID 35393493-Quinolinecarbonitrile, 4-hydroxy-

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
On this pageParticipantsProcedureWorkupSources & evidenceReaction notes
HCID 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-f9e34bda3027493b83d4e328ef761266
Source dataset
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06384051B1

Reaction notes

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