Water → HCID 135512543, compound

HRID 1469209Notes

Reaction equation

HRID 1469209 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH:11](=O)[CH2:12][CH2:13][CH2:14][CH3:15].O>CC(N(C)C)=O>[CH2:12]([C:11]1[NH:10][C:1](=[O:9])[C:2]2[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:4]=1)[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 6942AnthranilamideHCID 8063Pentanal

Product 1

HCID 135512543HCID 135512543, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Anthranilamide (300 mg, 2.20 mmol) was dissolved under argon in dimethylacetamide (5 ml), valeraldehyde (199 mg, 2.31 mmol) and Na2S2O5 (628 mg, 3.31 mmol) were added, and the mixture was stirred under reflux conditions for 4 h. After cooling to room temperature, water was added to the reaction mixture. By suction-filtering and thoroughly drying the solid formed, 2-butylquinazolin-4(3H)-one (254 mg, 54% of theory) was obtained as a colorless solid. 1H NMR (400 MHz, CDCl3 δ, ppm) 8.26 (d, 1H), 7.74 (dd, 1H), 7.69 (d, 1H), 7.46 (dd, 1H), 7.30 (br. s, 1H, NH), 2.75 (t, 2H), 1.82 (quint, 2H), 1.49 (sext, 2H), 1.00 (t, 3H).

Workup

  1. filtrationBy suction-filtering
  2. customthoroughly drying the solid
  3. customformed

Sources & evidence

ORD record
ord-e745f51339f541aca72476247e208228
Source dataset
uspto-grants-2015_04
Patent number
US09006265B2

Reaction notes

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