Water → HCID 86742187, compound

HRID 1253049Notes

Reaction equation

HRID 1253049 reaction equation
[CH:1]1[C:14]2[C:13](=[O:15])[C:12](=[N:16][OH:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.Cl[C:25]([O:27][CH3:28])=[O:26].O>CN(C)C=O.C(#N)C>[CH3:28][O:27][C:25]([O:17][N:16]=[C:12]1[C:13](=[O:15])[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:26]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6586Methyl chloroformateHCID 178516814HCID 178516814, compound

Product 1

HCID 86742187HCID 86742187, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent2×

Procedure

22.3 g (0.1 mole) of 9,10-phenanthrene-dione-9-oxime are dissolved in 200 ml of 1:1 mixture of dimethyl formamide and acetonitrile under stirring, whereupon 16 ml of pyridine are added. To the reaction mixture a solution of methyl chloroformate and 30 ml of acetonitrile is added dropwise under stirring. The reaction mixture is stirred first at room temperature for an hour and thereafter at boiling point for 15 minutes. The reaction mixture is cooled and poured into 700 ml of icecold water. On cooling the precipitated oily product solidifies. Thus 22.9 g of 9,10-phenanthrene-dione-9-methoxycarbonyl-oxime are obtained in the form of an orchre-yellow product. Yield 81.5%, mp.: 142°-143° C.

Workup

  1. additionare added
  2. stirringThe reaction mixture is stirred first at room temperature for an hour
  3. customfor 15 minutes
  4. temperatureThe reaction mixture is cooled
  5. temperatureOn cooling the precipitated oily product

Sources & evidence

ORD record
ord-5498f18f1023420d96ff5d3e9544932c
Source dataset
uspto-grants-1988_05
Patent number
US04746678

Reaction notes

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