Hydrochloric Acid → HCID 21952555, compound

HRID 1263453Notes

Reaction equation

HRID 1263453 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1COCC1.[CH2:14]([N:16]1[C:25]2[CH:24]=[CH:23][C:22]([CH:26]([CH3:28])[CH3:27])=[CH:21][C:20]=2[C:19](=[O:29])[C:18]2[C:30](=[O:37])[C:31]3[C:36]([C:17]1=2)=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH3:15].Cl>C(Cl)Cl>[CH2:14]([N:16]1[C:25]2[CH:24]=[CH:23][C:22]([CH:26]([CH3:28])[CH3:27])=[CH:21][C:20]=2[C:19](=[O:29])[C:18]2[C:30]([OH:37])([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:31]3[C:36]([C:17]1=2)=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 21952567HCID 21952567, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 21952555HCID 21952555, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2M solution of phenyl magnesium bromide in THF (1.07 mL, 1.87 mmol) was dissolved in anhydrous methylene chloride. To this solution was added dropwise a solution of 5-ethyl-8-isopropyl-5,10-dihydro-11H-indeno[1,2-b]quinolin-10,11-dione (500 mg, 1.58 mmol) in anhydrous methylene chloride with ice cooling and stirring followed by stirring at room temperature overnight. The reaction mixture was treated with 10% hydrochloric acid. The organic layer was separated, washed sequentially with diluted hydrochloric acid and saturated sodium chloride solution and dried with sodium sulfate followed by evaporation to remove methylene chloride. The title compound was isolated by subjecting the residue to silica gel-chromatography (chloroform) and crystallization from diethyl ether. 1H-NMR(CDCl3)δ 1.30(6H,d,CH(CH3)2), 1,79(3H,t,NCH2CH3), 3.05(1H,septet,CH), 4.81(2H,q,NCH2), 5.18(1H,s,H-11), 7.16-7.64(10H,m,Ar-H), 7.96(1H,d,H-6), 8.37(1H,d,H-9)

Workup

  1. stirringby stirring at room temperature overnight
  2. customThe organic layer was separated
  3. washwashed sequentially with diluted hydrochloric acid and saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. customfollowed by evaporation
  6. customto remove methylene chloride

Sources & evidence

ORD record
ord-bf7eaa81ce79426ab49da36eb175ff01
Source dataset
uspto-grants-2003_04
Patent number
US06541470B1

Reaction notes

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