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

HRID 1017536Notes

Reaction equation

HRID 1017536 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([NH2:18])=[O:17].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH:28]=O>CC(N(C)C)=O>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([C:28]2[NH:18][C:16](=[O:17])[C:15]3[C:14](=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:13]=2)[CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 6942AnthranilamideHCID 115693-MethoxybenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

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

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

p-Toluenesulfonic acid monohydrate (0.1 g, 0.3 mmol) was added to a solution of 2-aminobenzamide (30) (1.0 g, 7.3 mmol) and 3-methoxybenzaldehyde (34) (1.0 g, 7.3 mmol) in DMAC (20 ml). The mixture was stirred at room temperature 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 (70.0 mg, 4.0%) and 61 (1.7 g, 89.0%) as pale yellow powder.

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-d69670f5331340c5a233b5c83c88dc57
Source dataset
uspto-grants-2002_11
Patent number
US06479499B1

Reaction notes

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