Methyl cyanoacetate → HCID 22097616, compound

HRID 862630Notes

Reaction equation

HRID 862630 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[NH2:5][C:6]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)=O.[C:25]([CH2:27][C:28]([O:30][CH3:31])=[O:29])#[N:26]>O>[Cl:24][C:21]1[CH:20]=[C:7]2[C:6](=[CH:23][CH:22]=1)[N:5]=[C:25]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[N:26]=[C:8]2[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1

Participants

5

Reactant 3

HCID 7747Methyl cyanoacetateHCID 6451240Aluminum(III) ChlorideHCID 15592241HCID 15592241, compound

Product 1

HCID 22097616HCID 22097616, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Powdered aluminium chloride (0.21 g) was added to a mixture of 2-amino-5-chloro-3',4'-dimethoxybenzophenone (0.23 g) and methyl cyanoacetate (5 ml), and the resulting mixture was stirred at 100° C. for 2.5 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated. The residue was subjected to column chromatography on silica gel. The fractions eluted with hexane/ethyl acetate (4/1, v/v) gave methyl 6-chloro-4-(3,4-dimethoxyphenyl)quinazoline-2-acetate (0.161 g, 55%) which was then recrystallized from isopropyl ether. Colorless needles. mp. 144°-145° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated
  5. washThe fractions eluted with hexane/ethyl acetate (4/1

Sources & evidence

ORD record
ord-eda175d4ae504d7aa7ec78f229cf71e6
Source dataset
uspto-grants-1998_02
Patent number
US05719157

Reaction notes

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