Dichloromethane → HCID 136383550, compound

HRID 2305430Notes

Reaction equation

HRID 2305430 reaction equation
[C:1]1([N:7]2[C:16](=O)[C:15]3[C:14]([OH:18])=[C:13]4[C:19]5[C:32]([CH2:33][CH2:34][C:12]4=[CH:11][C:10]=3[CH:9]=[N:8]2)=[C:31]([O:35][CH3:36])[C:30]2[C:29](=[O:37])[C:28]3[C:23](=[CH:24][C:25](O)=[C:26]([CH3:39])[C:27]=3[OH:38])[C:22](=[O:41])[C:21]=2[C:20]=5[OH:42])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)Cl.[OH-:46].[Na+].[CH2:48](Br)[CH:49]=[CH2:50]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.Cl>[C:1]1([N:7]2[C:16](=[O:46])[C:15]3[C:14]([OH:18])=[C:13]4[C:19]5[C:32]([CH2:33][CH2:34][C:12]4=[CH:11][C:10]=3[CH:9]=[N:8]2)=[C:31]([O:35][CH3:36])[C:30]2[C:29](=[O:37])[C:28]3[C:23](=[CH:24][C:25]([CH2:50][CH:49]=[CH2:48])=[C:26]([CH3:39])[C:27]=3[OH:38])[C:22](=[O:41])[C:21]=2[C:20]=5[OH:42])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 135487800HCID 135487800, compound

Product 1

HCID 136383550HCID 136383550, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of 1 g (1.78 mmol) of 2-phenyl-10,12,15,16-tetrahydroxy-8-methoxy-11-methyl-9,14-dioxo-6,7,9,14-tetrahydronaphthaceno[1,2-g]phthalazin-1-one (5) in 10 m of CH2Cl2 are successively added, while stirring, at intervals of a few minutes 10 m of water, 10 mg of tetrabutylammonium bromide, 120 mg (3 mmol) of finely powdered sodium hydroxide and 0.26 m (2.8 mnmol) of allyl bromide. After 24 h at room temperature, the mixture is diluted with 40 m of water and acidifed with 10 per cent aqueous HCl. The organic phase is separated off, and the aqueous phase is extracted twice with 30 m of CH2Cl2. The combined organic phases are dried over MgSO4 and, without previous concentration, filtered through 20 g of silica gel 60, eluted with CH2Cl2 until colourless, and evaporated to dryness. 370 mg of the product are obtained. The yield is 35% of theory.

Workup

  1. customThe organic phase is separated off
  2. extractionthe aqueous phase is extracted twice with 30 m of CH2Cl2
  3. dry with materialThe combined organic phases are dried over MgSO4 and, without previous concentration
  4. filtrationfiltered through 20 g of silica gel 60
  5. washeluted with CH2Cl2 until colourless, and
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-f53f069a533c40cda8abfc229daec716
Source dataset
uspto-grants-2002_08
Patent number
US06440968B1

Reaction notes

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