Water → 3-Cyano-4-(4-methylphenyl)quinoline

HRID 274587Notes

Reaction equation

HRID 274587 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)=O.CO[CH:19](OC)[CH2:20][C:21]#[N:22].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[C:21]([C:20]1[CH:19]=[N:1][C:2]2[C:3]([C:4]=1[C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)=[CH:13][CH:14]=[CH:15][CH:16]=2)#[N:22]

Participants

6

Reactant 4

HCID 962WaterHCID 937313,3-DimethoxypropiononitrileHCID 1189232-Amino-4'-methylbenzophenone mHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 200929983-Cyano-4-(4-methylphenyl)quinoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-amino-4'-methylbenzophenone (10 g), 3,3-dimethoxypropionitrile (10.9 g), p-toluenesulfonic acid. monohydrate (1.0 g) in toluene (120 ml) was heated under reflux for 4 hours. After addition of water, the reaction mixture was extracted with ethyl acetate and the extract was concentrated to dryness. The residue was purified by column chromatography on silica gel. Recrystallization from isopropyl ether afforded pale yellow prisms (5.67 g, 49%), m.p. 96°-97° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. concentrationthe extract was concentrated to dryness
  5. customThe residue was purified by column chromatography on silica gel
  6. customRecrystallization from isopropyl ether afforded pale yellow prisms (5.67 g, 49%), m.p. 96°-97° C.

Sources & evidence

ORD record
ord-3248594dec474d789b0425c7105cf359
Source dataset
uspto-grants-1995_02
Patent number
US05389641

Reaction notes

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