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3,5-Dimethoxybenzaldehyde → 6-amino-2-(3,5-dimethoxy-phenyl)-3H-quinazolin-4-one

HRID 591863
Notes
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Reaction equation

HRID 591863 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([O:24][CH3:25])[CH:23]=1)[CH:19]=O.S([O-])(O)=O.[Na+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CN(C)C(=O)C>[NH2:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[N:1]=[C:19]([C:18]1[CH:21]=[C:22]([O:24][CH3:25])[CH:23]=[C:16]([O:15][CH3:14])[CH:17]=1)[NH:6][C:4]2=[O:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 817473,5-DimethoxybenzaldehydeHCID 976652-Amino-5-nitrobenzamideHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 23665763Sodium Bisulfite

Product 1

HCID 1363480626-amino-2-(3,5-dimethoxy-phenyl)-3H-quinazolin-4-one

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-amino-5-nitro-benzamide (1.81 g, 10.0 mmol), 3,5-dimethoxy-benzaldehyde (1.83 g, 11.0 mmol), sodium hydrogen sulfite (58.5 wt %, 3.94 g, 22.0 mmol), and p-toluenesulfonic acid monohydrate (0.38 g, 2.00 mmol) in N,N-dimethylacetamide (20 mL) was stirred at 150° C. for 17 hours under nitrogen and then cooled to room temperature. Saturated aqueous NaHCO3 (approximately 1 mL) was added. The mixture was stirred at room temperature for 2 hours, then concentrated to dryness. Water (80 mL) was added, stirred for 0.5 hours, and filtered. The solid was air dried. The crude compound was purified by column chromatography (silica gel 230-400 mesh; ethyl acetate as eluent) to give 6-amino-2-(3,5-dimethoxy-phenyl)-3H-quinazolin-4-one as a yellow solid. Yield: 1.50 g (50%).

Workup

  1. temperaturecooled to room temperature
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. concentrationconcentrated to dryness
  4. additionWater (80 mL) was added
  5. stirringstirred for 0.5 hours
  6. filtrationfiltered
  7. customdried
  8. customThe crude compound was purified by column chromatography (silica gel 230-400 mesh; ethyl acetate as eluent)

Sources & evidence

ORD record
ord-e939b15943194a47b7530321302338fb
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09238640B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes