Triethylamine → 2-(1-Acetylindol-3-yl)-5,5-dimethylcyclohexane-1,3-dione

HRID 1162167Notes

Reaction equation

HRID 1162167 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=O)[CH2:5]1)(=[O:3])[CH3:2].[CH3:14][C:15]1([CH3:23])[CH2:20][C:19](=[O:21])[CH2:18][C:17](=[O:22])[CH2:16]1.C(N(CC)CC)C>C(O)(=O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:18]2[C:19](=[O:21])[CH2:20][C:15]([CH3:23])([CH3:14])[CH2:16][C:17]2=[O:22])=[CH:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31358DimedoneHCID 5388191-Acetyl-1,2-dihydro-3H-indol-3-one

Product 1

HCID 7947322-(1-Acetylindol-3-yl)-5,5-dimethylcyclohexane-1,3-dioneYield 76%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-Acetyl-1,2-dihydroindol-3-one of Example 1d (131.3 g, 0.75 mol) and 5,5-dimethyl-cyclohexane-1,3-dione (105 g, 0.75 mol) were added to a mixture of acetic acid (700 mL) and triethylamine (105 mL, 0.75 mol) at room temperature under stirring. The reaction mixture was refluxed for 6 h. About ⅓ volume of solvents was removed in vacuum, and the mixture was cooled and diluted with water (50 mL). The precipitate was filtered off, washed with ethanol-water, 1:1 and dried to afford 169.4 g (76%) of colorless crystals; m.p. 225-227° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. customAbout ⅓ volume of solvents was removed in vacuum
  3. temperaturethe mixture was cooled
  4. additiondiluted with water (50 mL)
  5. filtrationThe precipitate was filtered off
  6. washwashed with ethanol-water, 1:1
  7. customdried

Sources & evidence

ORD record
ord-2380ebeec3794999b46bf5e137079642
Source dataset
uspto-grants-2010_10
Patent number
US07820691B2

Reaction notes

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