Tetrahydrofuran → 3-(4-Nitro-pyridin-2-ylmethylene)-3H-isobenzofuran-1-one

HRID 600265Notes

Reaction equation

HRID 600265 reaction equation
COP([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])NN=1)(=O)OC.[N+:18]([C:21]1[CH:26]=[CH:25][N:24]=[C:23]([CH:27]=O)[CH:22]=1)([O-:20])=[O:19].C(N(CC)CC)C.C1C[O:39]CC1>O>[N+:18]([C:21]1[CH:26]=[CH:25][N:24]=[C:23]([CH:27]=[C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7](=[O:39])[O:17]2)[CH:22]=1)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 145789294-NitropicolinaldehydeHCID 86628633(4-Oxo-3,4-dihydro-phthalazin-1-yl)-phosphonic acid dimethyl ester

Product 1

HCID 689120253-(4-Nitro-pyridin-2-ylmethylene)-3H-isobenzofuran-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cooled solution of (4-oxo-3,4-dihydro-phthalazin-1-yl)-phosphonic acid dimethyl ester (0.202 g, 0.837 mmol) in THF (4 mL) at 10° C. was added 4-nitro-pyridine-2-carbaldehyde (0.837 mmol) under a nitrogen atmosphere. Triethylamine (0.174 mL, 1.25 mmol) was added dropwise over 10 minutes and then allowed to stir at room temperature for 18 hours. The yellow suspension was poured in water (9 mL), and the then filtered, the solid was washed with water (2×2 mL), hexane (2×2 mL) and then diethyl ether (2×2 mL) and then dried in vacuo to afford a 0.73 g of the desired products. Two peaks in LC-MS analysis, (0.13 g, 18% two steps) and required no further purification, m/z (LC-MS, ESP), RT=4.26 mins (M+H) 269, & RT=4.52 mins (M+H) 269.

Workup

  1. filtrationthe then filtered
  2. washthe solid was washed with water (2×2 mL), hexane (2×2 mL)
  3. dry with materialdiethyl ether (2×2 mL) and then dried in vacuo

Sources & evidence

ORD record
ord-af046cb2823e4619bf45a8f2c7832825
Source dataset
uspto-grants-2011_03
Patent number
US07902193B2

Reaction notes

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