Ethyl orthoformate → 7-Methyl-4(3H)-quinazolinone

HRID 1469758Notes

Reaction equation

HRID 1469758 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH:12](OCC)(OCC)OCC>>[CH3:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:5])[NH:6][CH:12]=[N:1]2)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 28014742-Amino-4-methylbenzamide

Product 1

HCID 1354525337-Methyl-4(3H)-quinazolinone

Conditions

Temperature
110 °C

Procedure

A suspension of 2-amino-4-methylbenzamide (1.2 g, 8.0 mmol) in CH(OEt)3 (10 mL) was heated in a sealed tube at 110° C. for 4 h. Then the reaction was quenched with aq. NaHCO3 solution at rt and the precipitate obtained was filtered and dried. The solid mass was purified by column chromatography to afford 1.1 g of the title product. 1H NMR (300 MHz, DMSO-d6): δ 12.14 (br s, 1H), 8.05 (s, 1H), 8.00 (d, J=7.8 Hz, 1H), 7.47 (s, 1H), 7.34 (d, J=7.8 Hz, 1H), 2.45 (s, 3H).

Workup

  1. customThen the reaction was quenched with aq. NaHCO3 solution at rt
  2. customthe precipitate obtained
  3. filtrationwas filtered
  4. customdried
  5. customThe solid mass was purified by column chromatography

Sources & evidence

ORD record
ord-8d237628db994d84a4ab7d2c51eac94a
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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