2-Hydroxybenzonitrile → HCID 16244409, compound

HRID 1363197Notes

Reaction equation

HRID 1363197 reaction equation
O=[C:2]1[C:11]2[C:6](=[C:7]([C:12]#[N:13])[CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.OC1C=CC=CC=1C#[N:18].C([O-])(=O)C.[NH4+]>CO>[NH2:18][CH:2]1[C:11]2[C:6](=[C:7]([C:12]#[N:13])[CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 119072-HydroxybenzonitrileHCID 517165Ammonium AcetateHCID 55274142HCID 55274142, compound

Product 1

HCID 16244409HCID 16244409, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 260 mg of 4-oxo-3,4-dihydro-2H-chromene-8-carbonitrile (made from 2-hydroxybenzonitrile via the procedure described in Example 29), ammonium acetate (1.2 g), and 3 A molecular sieves (1.5 g) in 10 mL of methanol was stirred for 5 days. The mixture was filtered through celite and the filtrate concentrated in vacuo. The crude residue was treated with 100 mL of 1 M HCl and extracted with ethyl ether (3×100 mL). The aqueous layer was made basic to pH 10 with saturated NaOH and extracted with DCM (3×100 mL). The combined DCM layers were washed with brine, dried over magnesium sulfate, and concentrated in vacuo to provide 150 mg of the title compound.

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate concentrated in vacuo
  3. additionThe crude residue was treated with 100 mL of 1 M HCl
  4. extractionextracted with ethyl ether (3×100 mL)
  5. extractionextracted with DCM (3×100 mL)
  6. washThe combined DCM layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-943315e30bed44209a93f54775a51aa4
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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