Formic Acid → HCID 178439036, compound

HRID 386974Notes

Reaction equation

HRID 386974 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=O.[CH:9]([C:12]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([CH3:21])[CH3:20])[C:13]=1[NH2:14])([CH3:11])[CH3:10].C(O)=O>CO>[CH:9]([C:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:19]([CH3:21])[CH3:20])[C:2]=1[NH:14][C:13]1/[C:15](=[N:14]/[C:13]2[C:12]([CH:9]([CH3:11])[CH3:10])=[CH:18][CH:17]=[CH:16][C:15]=2[CH:19]([CH3:21])[CH3:20])/[CH2:16][CH2:17][CH2:18][CH:12]=1)([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 130061,2-CyclohexanedioneHCID 32484Diisopropylaniline

Product 1

HCID 178439036HCID 178439036, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Synthesis based on literature procedure (Gates, D. P.; Svejda, S. A. Onate, E.; Killian, C. M.; Johnson, L. K.; White, P. S.; Brookhart M. Macromolecules, 2000; 33:2320-2334.). Cyclohexane-1,2-dione (2.062 g, 18.39 mmol) and 2,6-diisopropylaniline (6.52 g, 36.78 mmol) are dissolved in 70 mL of methanol. To this solution is added 1 mL of formic acid and the mixture is stirred for 3 days at room temperature. Precipitated white crystalline solid is collected on the frit, washed with methanol (2×15 mL) and dried under reduced pressure to give 4.1 g (51.8% yield) of title compound of Preparation 1.

Workup

  1. customSynthesis
  2. customPrecipitated white crystalline solid
  3. customis collected on the frit
  4. washwashed with methanol (2×15 mL)
  5. customdried under reduced pressure
  6. customto give

Sources & evidence

ORD record
ord-4d6c9881c1434e48a9e9a4214ee3fcc1
Source dataset
uspto-grants-2013_02
Patent number
US08372927B2

Reaction notes

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