1,3-Dioxolane, 2-[(4-nitrophenyl)methyl]- → HCID 14858790, compound

HRID 2081949Notes

Reaction equation

HRID 2081949 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]2[O:15][CH2:14][CH2:13][O:12]2)=[CH:6][CH:5]=1)([O-])=O>CO>[O:12]1[CH2:13][CH2:14][O:15][CH:11]1[CH2:10][C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 114015441,3-Dioxolane, 2-[(4-nitrophenyl)methyl]-

Product 1

HCID 14858790HCID 14858790, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound III (231 mg), from Example 6, was dissolved in methanol (about 3 ml) and the mixture flushed with nitrogen. Pd/C (120 mg) was added to the mixture and the sides of the reaction flask were rinsed with methanol (about 2 ml). The mixture was flushed with nitrogen and then flushed with hydrogen. The reaction mixture was stirred for 45 minutes, and then filtered through Celite. The Celite was rinsed several times with methanol and the filtrate and rinses were rotoevaporated to yield 184.4 mg (90.6 percent yield) of Compound IV.

Workup

  1. customthe mixture flushed with nitrogen
  2. additionPd/C (120 mg) was added to the mixture
  3. washthe sides of the reaction flask were rinsed with methanol (about 2 ml)
  4. customThe mixture was flushed with nitrogen
  5. customflushed with hydrogen
  6. filtrationfiltered through Celite
  7. washThe Celite was rinsed several times with methanol

Sources & evidence

ORD record
ord-c6d059a7a06041d68526be938923b8f4
Source dataset
uspto-grants-1993_02
Patent number
US05187086

Reaction notes

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