2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 178487734, compound

HRID 1852085Notes

Reaction equation

HRID 1852085 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[N:20]=[C:19]([OH:21])[C:18]3[C:13](=[CH:14][C:15]([O:22][CH3:23])=[CH:16][CH:17]=3)[NH:12]2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:20]=[C:19]([OH:21])[C:18]3[C:13](=[CH:14][C:15]([O:22][CH3:23])=[CH:16][CH:17]=3)[N:12]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 178487280HCID 178487280, compound

Product 1

HCID 178487734HCID 178487734, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(4-isopropoxyphenyl)-7-methoxy-1,2-dihydroquinazolin-4-ol (685 mg, 2.193 mmol) was dissolved in DCM (10 mL) followed by the addition of DDQ (597 mg, 2.63 mmol). The reaction was stirred for 1 h. The reaction was diluted with DCM and filtered through celite. The filtrate was collected and concentrated under vacuum. The crude material was purified by silica gel chromatography using 40% EtOAc in hexanes. The product fractions were collected and the solvent removed under vacuum to give 2-(4-isopropoxyphenyl)-7-methoxyquinazolin-4-ol (495, 73% yield). MS: MS m/z 311.1 (M++1).

Workup

  1. filtrationfiltered through celite
  2. customThe filtrate was collected
  3. concentrationconcentrated under vacuum
  4. customThe crude material was purified by silica gel chromatography
  5. customThe product fractions were collected
  6. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-46b7330135264bd1a2cc24e6dd4e621d
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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