Acetic Acid → HCID 14010095, compound

HRID 1788781Notes

Reaction equation

HRID 1788781 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[O:12][C:13](=[CH2:17])[C:14]([OH:16])=[O:15].[C:18]1([C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N+]=[N-])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O)(=O)C>C(#N)C>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[O:12][C:13](=[CH2:17])[C:14]([O:16][CH:24]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 612301,1'-(Diazomethylene)bis(benzene)3×HCID 19752204HCID 19752204, compound

Product 1

HCID 14010095HCID 14010095, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-[(1,3-Dioxo-2H-isoindol-2-yl)oxy]-2-propenoic acid (1.54 g, 4.8 mmole) was dissolved in 25 ml of acetonitrile and a solution of diphenyldiazomethane (1.17 g, 5.94 mmole/50 ml acetonitrile) was added dropwise. After approximately 1.1 equivalents of diphenyldiazomethane had been added, tlc showed no starting material remaining. The excess diphenyldiazomethane was decomposed with the addition of a small amount of acetic acid. The reaction solution was concentrated to a residue, dissolved in ethyl acetate, washed consecutively with 1N sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and evaporated to a solid. After trituration with hexane, 1.9 g of the title compound was obtained.

Workup

  1. concentrationThe reaction solution was concentrated to a residue
  2. dissolutiondissolved in ethyl acetate
  3. washwashed consecutively with 1N sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated to a solid

Sources & evidence

ORD record
ord-d903185401c6425592f4f674eacdfc7e
Source dataset
uspto-grants-1987_08
Patent number
US04684722

Reaction notes

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