Triethyl orthoacetate → 4(3H)-Quinazolinone, 2-methyl-3-(2-pyridyl)-

HRID 1367654

Reaction equation

HRID 1367654 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:5].[CH2:17](OC(OCC)(OCC)C)[CH3:18]>O>[CH3:17][C:18]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[C:4](=[O:5])[C:3]2[C:2](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:1]=1

Participants

4

Reactant 2

HCID 66221Triethyl orthoacetateHCID 2763252-amino-N-(pyridin-2-yl)benzamide

Product 1

HCID 640494(3H)-Quinazolinone, 2-methyl-3-(2-pyridyl)-Yield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 72 (3 g, 0.015 mol) and 1,1,1-triethoxy-ethane (5 g, 0.045 mol) were heated for 7 hours. The reaction mixture was poured into water, filtered, and the precipitate was washed with water and recrystallized from EtOH to yield 73 (2.5 g, 75%). M. Wt. 237. LCMS [M+H]+=238.

Workup

  1. temperaturewere heated for 7 hours
  2. filtrationfiltered
  3. washthe precipitate was washed with water
  4. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-52413c69eb47490895aba0999c6e30a4
Source dataset
uspto-grants-2011_02
Patent number
US07893260B2

Linked notes

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