2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-(6-Methoxypyridin-3-yl)-1,3-benzoxazol-6-ol

HRID 2241822Notes

Reaction equation

HRID 2241822 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=[N:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=2[OH:18])=[CH:5][CH:4]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[O:18][C:12]3[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:11]=3[N:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 592038424-([(6-Methoxypyridin-3-yl)methylene]amino}benzene-1,3-diol

Product 1

HCID 247808042-(6-Methoxypyridin-3-yl)-1,3-benzoxazol-6-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-{[(6-methoxypyridin-3-yl)methylene]amino}benzene-1,3-diol was dissolved in CH2Cl2 (30 mL) and DDQ was added. The reaction mixture was stirred over night at r.t., SiO2 was added and the solvents were removed under reduced pressure. The crude product was purified by flash column chromatography to give the title compound (189.1 mg). 1H NMR δ ppm 9.88 (s, 1H) 8.90 (dd, 1H) 8.35 (dd, 1H) 7.56 (d, 1H) 7.09 (d, 1H) 6.85 (dd, 1H) 3.95 (s, 3H); MS m/z 243 (M+H).

Workup

  1. additionSiO2 was added
  2. customthe solvents were removed under reduced pressure
  3. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-9e490c376a294c6b9abad52ed81ec33c
Source dataset
uspto-grants-2010_03
Patent number
US07670591B2

Reaction notes

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