Water → 3-Deoxyviridicatin

HRID 1199661Notes

Reaction equation

HRID 1199661 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17].[H-].[Na+].O>O1CCCC1.CN(C)C=O>[O:18]=[C:16]1[CH:17]=[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]2[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=2)[NH:1]1

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 760802-Aminobenzophenone

Product 1

HCID 3759123-Deoxyviridicatin

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of o-amino benzophenone (10 g) and acetic acid anhydride (10 ml) in tetrahydrofuran (150 ml) was refluxed for 8 hours. The mixture was thereafter evaporated and the residue was partitioned between sat NaHCO3, (20 ml) and diethylether (150 ml). The organic phase was dried and evaporated to give a yellow oil which was redissolved in dimethyl formamide (150 ml). To this solution was added NaH (5 g) and the mixture was stirred at 110° C. for 11/2 hour, whereafter it was cooled to room temperature, and poured into water (300 ml). This treatment afforded a precipitate of the title compound as pale crystals, which were collected by filtration. The crystals were washed with water and dried. M.p. 244°-247° C.

Workup

  1. temperaturewas refluxed for 8 hours
  2. customThe mixture was thereafter evaporated
  3. customthe residue was partitioned
  4. customThe organic phase was dried
  5. customevaporated
  6. customto give a yellow oil which
  7. temperaturewhereafter it was cooled to room temperature

Sources & evidence

ORD record
ord-966424492da34cceb21e6670cc38ba01
Source dataset
uspto-grants-1990_02
Patent number
US04902686

Reaction notes

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