Acetic Acid → HCID 23649407, compound

HRID 1985600Notes

Reaction equation

HRID 1985600 reaction equation
[CH3:1][C:2]([CH3:17])([CH3:16])[CH2:3][C:4](=O)[CH2:5][C:6]1[C:7](=O)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=1.O.O.[NH2:20][NH2:21].C(O)(=O)C>C(O)C>[CH3:1][C:2]([CH3:17])([CH3:16])[CH2:3][C:4]1[N:21]=[N:20][C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 25112586(Z)-2-(4,4-dimethyl-2-oxo-pentyl)-cyclooct-2-enone

Product 1

HCID 23649407HCID 23649407, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
105 °C

Procedure

A solution of (Z)-2-(4,4-Dimethyl-2-oxo-pentyl)-cyclooct-2-enone (0.07 g) in ethanol (6 ml) was treated at RT with water (1.5 ml), hydrazine monohydrate (0.07 ml) and acetic acid (1.5 ml), and the mixture was then heated to reflux for 12 h (oil bath temperature: 105° C.). The reaction mixture was partitioned between water and AcOEt. The combined organic layers were washed with 2M aqueous KHCO3, dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (heptane/AcOEt 100% to 85%) to give 3-(2,2-dimethyl-propyl)-5,6,7,8,9,10-hexahydro-cycloocta[c]pyridazine, (0.018 g) as an amorphous white solid. MS (ESI): 233.2 (MH+).

Workup

  1. temperaturethe mixture was then heated
  2. customThe reaction mixture was partitioned between water and AcOEt
  3. washThe combined organic layers were washed with 2M aqueous KHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography (heptane/AcOEt 100% to 85%)

Sources & evidence

ORD record
ord-a414f04a4e90423fafc91acb1deca6e8
Source dataset
uspto-grants-2009_06
Patent number
US07547697B2

Reaction notes

Loading…