Anthranilamide → 2-(3-methoxyphenyl)quinazolin-4(3H)-one

HRID 1017535Notes

Reaction equation

HRID 1017535 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O>CC(N(C)C)=O>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([C:16]2[NH:6][C:4](=[O:5])[C:3]3[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:1]=2)[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 6942AnthranilamideHCID 115693-Methoxybenzaldehyde

Product 1

HCID 1354863992-(3-methoxyphenyl)quinazolin-4(3H)-oneYield 16.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2-Aminobenzamide (30) (1.0 g, 7.3 mmol) and 3-methoxybenzaldehyde (34) (1.0 g, 7.3 mmol) were heated with stirring in DMAC (20 ml) at 80° C. for 2 h and then poured into ice water (200 ml). The precipitate was collected, washed with water, then dried and purified by column chromatography (silica gel-ethyl acetate/n-hexane) to afford 43 (0.3 g, 15.0%) and 61 (1.4 g, 75.2%) as pale yellow powder. Yield, mp, and spectral data are given in Table 1.

Workup

  1. customThe precipitate was collected
  2. washwashed with water
  3. customdried
  4. custompurified by column chromatography (silica gel-ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-e7836cef411d4e559316193769bcd575
Source dataset
uspto-grants-2002_11
Patent number
US06479499B1

Reaction notes

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