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Methyl cyanoacetate → 6,7-Dimethoxy-4-(3,4-dimethoxyphenyl)quinazoline-2-acetic acid methyl ester

HRID 1584144
Notes
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Reaction equation

HRID 1584144 reaction equation
[NH2:1][C:2]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[CH:16][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1)=O.[CH3:24][O:25][C:26](=[O:30])[CH2:27][C:28]#[N:29].[Cl-].[Al+3].[Cl-].[Cl-]>O>[CH3:24][O:25][C:26](=[O:30])[CH2:27][C:28]1[N:29]=[C:4]([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=2)[C:3]2[C:2](=[CH:19][C:18]([O:20][CH3:21])=[C:17]([O:22][CH3:23])[CH:16]=2)[N:1]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7747Methyl cyanoacetateHCID 6451240Aluminum(III) ChlorideHCID 99269672-Amino-4,5,3',4'-tetramethoxybenzophenone

Product 1

HCID 212240726,7-Dimethoxy-4-(3,4-dimethoxyphenyl)quinazoline-2-acetic acid methyl esterYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone (6.3 g) and cyanoacetic acid methyl ester (23 ml), powdered aluminum chloride (5.3 g) was added, followed by stirring at 100° C. for 2.5 hours. The reaction mixture was poured over water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), after which the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (4:1, v/v) to yield 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinazoline-2-acetic acid methyl ester (4.4 g, 55%), which was then recrystallized from isopropyl ether to yield a colorless needle crystal having a melting point of 152 to 153° C.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationafter which the solvent was distilled off
  6. washeluted with hexane-ethyl acetate (4:1

Sources & evidence

ORD record
ord-98691ea0ef2f41838193c7fb9362d523
Source dataset
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05932592

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes