1,3-Cyclohexanedione → HCID 178515920, compound

HRID 1013834Notes

Reaction equation

HRID 1013834 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.C(OC([N:18]([CH3:20])C)N(C)C)(C)(C)C.Cl.Cl.[NH2:23]N>C(O)=O>[N:23]1[NH:18][CH:20]=[C:2]2[C:1]=1[CH2:6][CH2:5][CH2:4][C:3]2=[O:7]

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 17548Hydrazine, dihydrochlorideHCID 79885tert-Butoxy bis(dimethylamino)methane

Product 1

HCID 178515920HCID 178515920, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To 1,3-cyclohexane dione (22.4 g, 0.19 mol), add tert-butoxybis(dimethylamino)methane (23.1 g, 0.19 mol). Stir the reaction at room temperature for 5 minutes. Add hydrazine dihydrochloride (20.55 g, 0.19 mol) to the reaction and stir at room temperature for 1 hour. Add formic acid (50 mL) to the mixture. Bring the reaction to 100° C. and stirred for 2 hours. Cool the reaction and extract with 3:1 chloroform:IPA (10×60 mL each). Combine the organics and dry over sodium sulfate. After filtration and concentration, load the residue on silica gel column and flash with ethyl acetate to afford 21.6 g (82%) of the desired product as white-grey solid. NMR matches the structure. MS (m/z): 137 [M+H]+.

Workup

  1. customthe reaction at room temperature for 5 minutes
  2. stirringstir at room temperature for 1 hour
  3. customBring the reaction to 100° C.
  4. stirringstirred for 2 hours
  5. temperatureCool
  6. customthe reaction
  7. extractionextract with 3:1 chloroform
  8. dry with materialCombine the organics and dry over sodium sulfate
  9. filtrationAfter filtration and concentration, load the residue on silica gel column and flash with ethyl acetate

Sources & evidence

ORD record
ord-426b13bedd7e43b9984b33fdad29d9c6
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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