Benzene → 2-(1,3-Dioxo-2-azaindan-2-yl)-4-methyl-1-phenylpentan-1-one

HRID 236404Notes

Reaction equation

HRID 236404 reaction equation
S(Cl)(Cl)=O.[O:5]=[C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[N:7]1[CH:16]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:17]([OH:19])=O.[CH:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(O)C.CCCCCC>[O:15]=[C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6](=[O:5])[N:7]1[CH:16]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:17]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:19]

Participants

7

Reactant 4

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 1028082-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-methylpentanoic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 197916912-(1,3-Dioxo-2-azaindan-2-yl)-4-methyl-1-phenylpentan-1-oneYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Procedure

Thionyl chloride (34.8 ml, 480 mmol) was added to a mixture of 2-(1,3-dioxo-2-azaindane-2-yl)-4-methylpentanoic acid (83.61 g, 320 mmol) and benzene (320 ml). The resulting mixture was heated under reflux for 2 hours. The solvent and excess thionyl chloride were removed by distillation under reduced pressure, followed by addition of benzene (320 ml). The benzene was removed and fresh benzene (480 ml) was added to form a solution. Anhydrous aluminum chloride (106.7 g, 800 mmol) was added immediately to the solution and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into ice water (700 ml). The aqueous layer was extracted with benzene (200 ml). After being washed first with water and then with an aqueous sodium bicarbonate solution and with brine, the combined organic layer was dried over sodium sulfate and then evaporated under reduced pressure. The residue was treated with ethanol to obtain crystals. The crystals were dissolved with heating in ethanol (80 ml) and added with hexane (160 ml). Precipitated crystals were collected by filtration and washed first with a 1:2 mixed solution (240 ml) of ethanol and hexane and then with hexane. The crystals were dried in air to obtain 74.6 g of the intended compound as white crystals (yield: 73%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customThe solvent and excess thionyl chloride were removed by distillation under reduced pressure
  4. additionfollowed by addition of benzene (320 ml)
  5. customThe benzene was removed
  6. additionfresh benzene (480 ml) was added
  7. customto form a solution
  8. extractionThe aqueous layer was extracted with benzene (200 ml)
  9. washAfter being washed first with water
  10. dry with materialwith an aqueous sodium bicarbonate solution and with brine, the combined organic layer was dried over sodium sulfate
  11. customevaporated under reduced pressure
  12. additionThe residue was treated with ethanol
  13. customto obtain crystals
  14. dissolutionThe crystals were dissolved
  15. customPrecipitated crystals
  16. filtrationwere collected by filtration
  17. washwashed first with a 1:2 mixed solution (240 ml) of ethanol and hexane
  18. customThe crystals were dried in air

Sources & evidence

ORD record
ord-5fdf054b22fa4d7c991ab112212662b6
Source dataset
uspto-grants-1987_02
Patent number
US04644063

Reaction notes

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