Sodium hydride → HCID 67884120, compound

HRID 1613600Notes

Reaction equation

HRID 1613600 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[H-].[Na+].[O:13]1[CH:20]2[CH:14]1[CH2:15][CH2:16][O:17][C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=12>CN1C(=O)N(C)CCC1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2](=[O:1])[N:3]([C@@H:20]2[C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[O:17][CH2:16][CH2:15][C@H:14]2[OH:13])[CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 13149080HCID 13149080, compoundHCID 178526703HCID 178526703, compound

Product 1

HCID 67884120HCID 67884120, compound

Reagents, catalysts & solvents 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent2×

Conditions

Temperature
95 °C

Procedure

7.85 g (56 mmol) of 2-hydroxy-5-nitro-pyridine are added in portions to 1.61 g (56 mmol) of sodium hydride (80% dispersion in mineral oil) in 30 ml of DMPU (1,3-dimethyl-tetrahydro-2(1H)-pyrimidinone) under argon. After evolution of gas has ceased the mixture is stirred for 20 minutes. Then, at room temperature, a solution of 4,5-epoxy-2,3,4,5-tetrahydro-1-benzoxepin in 10 ml of DMPU is added dropwise. The mixture is subsequently heated at 95° C. for 6 hours. The mixture is poured into ice/water, stirring vigorously, and precipitated solid is filtered off with suction. The solid is chromatographed on silica gel (ethyl acetate/cyclohexane 2:1), and the pale yellow oil obtained in this way is crystallized in methyl tert.-butyl ether. Melting point 152°-155° C.

Workup

  1. stirringstirring vigorously
  2. customprecipitated solid
  3. filtrationis filtered off with suction
  4. customThe solid is chromatographed on silica gel (ethyl acetate/cyclohexane 2:1)
  5. customthe pale yellow oil obtained in this way
  6. customis crystallized in methyl tert.-butyl ether

Sources & evidence

ORD record
ord-8ae5685c517d4a3d8488f10ef82c1a1a
Source dataset
uspto-grants-1993_03
Patent number
US05194442

Reaction notes

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