2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 4-Hydroxy-2-(pyridin-4-yl)quinazoline, 4-(4-Hydroxyquinazolin-2-yl)pyridine

HRID 2357878Notes

Reaction equation

HRID 2357878 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[N:11]1[CH:16]=[CH:15][C:14]([CH:17]=O)=[CH:13][CH:12]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>CO>[N:11]1[CH:16]=[CH:15][C:14]([C:17]2[NH:10][C:1](=[O:9])[C:2]3[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:4]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 6942AnthranilamideHCID 133894-Pyridinecarboxaldehyde

Product 1

HCID 1354126684-Hydroxy-2-(pyridin-4-yl)quinazoline, 4-(4-Hydroxyquinazolin-2-yl)pyridineYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a flask of anthranilamide (1 mmol) was added 4-pyridine carboxaldehyde (1 mmol) to form a paste. Followed by the careful addition of 2,3 dichloro-5,6-dicyano-1,4-benzoquinone, (0.5 mmol), the well blended mixture was microwaved in a beaker with silica for 9 min. To the resultant solid was added methanol with subsequent sonication. The collected filtrate was concentrated and dried in vacuo to afford the desired product as a brown solid (85% yield). 1H NMR (400 MHz, d6-DMSO): δ 12.80 (br s, 1H), 8.80 (d, 2H), 8.20 (d, 1H), 8.12 (d, 2H), 7.88 (t, 1H), 7.80 (d, 1H), 7.60 (t, 1H). MS (EI) for C13H9N3O: 224 (MH+).

Workup

  1. customto form a paste
  2. customthe well blended mixture was microwaved in a beaker with silica for 9 min
  3. customwith subsequent sonication
  4. concentrationThe collected filtrate was concentrated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-b54523dfdfb044589984406ca9abb7bd
Source dataset
uspto-grants-2010_07
Patent number
US07763627B2

Reaction notes

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