1,2-Dichloroethane → HCID 131714819, compound

HRID 364214Notes

Reaction equation

HRID 364214 reaction equation
[ClH:1].[CH2:2]([N:4]([CH2:27][CH3:28])[CH2:5][CH2:6][N:7]1[C:15]2[CH:14]=[CH:13][C:12]([N+:16]([O-])=O)=[C:11]3[Se:19][C:20]4[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][C:21]=4[C:9]([C:10]=23)=[N:8]1)[CH3:3].Br[CH2:30][CH2:31][N:32]1C(=O)C2=CC=CC=C2C1=O.[Cl:43]CCCl.C(N(C(C)C)CC)(C)C>[Pd].CN(C)C=O.ClCCl>[ClH:43].[ClH:1].[ClH:43].[NH2:32][CH2:31][CH2:30][NH:16][C:12]1[CH:13]=[CH:14][C:15]2[N:7]([CH2:6][CH2:5][N:4]([CH2:27][CH3:28])[CH2:2][CH3:3])[N:8]=[C:9]3[C:21]4[CH:22]=[C:23]([OH:26])[CH:24]=[CH:25][C:20]=4[Se:19][C:11]=1[C:10]=23

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 81531DiisopropylethylamineHCID 131714820HCID 131714820, compound

Product 1

HCID 131714819HCID 131714819, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 4.28 g (0.009 mole) of 2-[2-(diethylamino)ethyl]-5-nitro-2H-[1]benzoselenino[4,3,2-cd]indazol-9-ol, hydrochloride and 0.650 g of 20% palladium on carbon in 100 ml N,N-dimethylformamide is hydrogenated at atmospheric pressure for 13 hours. An additional 0.25 g of catalyst is added and the hydrogenation continues for another 24 hours. The mixture is filtered through a Celite pad and the filtrate is concentrated in vacuo to 4.74 g of a dark orange-brown oil. To this oil is added 2.67 g (0.011 mole) of N-(2-bromoethyl)phthalimide and the mixture is heated under argon in a 110° C. oil bath for 20 hours. To the resulting solid is added 200 ml of 1,2-dichloroethane and 3.3 ml of diisopropylethylamine. The mixture is heated under reflux in an argon atomosphere for two hours, diluted further with dichloromethane, and washed once with a saturated solution of aqueous sodium bicarbonate. The organic layer is separated, dried over sodium sulfate, filtered, and concentrated to a crude solid. The solid is dissolved in dichloromethane and filtered through a small column of Florisil with a 1:9 (v/v) solution of methanol and 1,2-dichloroethane. The effluent is concentrated and the resulting solid is triturated with hot 2-propanol to give 1.98 g of the dried product; mp 203°-205° C.

Workup

  1. waitthe hydrogenation continues for another 24 hours
  2. filtrationThe mixture is filtered through a Celite pad
  3. concentrationthe filtrate is concentrated in vacuo to 4.74 g of a dark orange-brown oil
  4. temperatureThe mixture is heated
  5. temperatureunder reflux in an argon atomosphere for two hours
  6. washwashed once with a saturated solution of aqueous sodium bicarbonate
  7. customThe organic layer is separated
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to a crude solid
  11. dissolutionThe solid is dissolved in dichloromethane
  12. filtrationfiltered through a small column of Florisil with a 1:9 (v/v) solution of methanol and 1,2-dichloroethane
  13. concentrationThe effluent is concentrated
  14. customthe resulting solid is triturated with hot 2-propanol

Sources & evidence

ORD record
ord-a4813f24f6564fabbb81198e2bff16ed
Source dataset
uspto-grants-1986_08
Patent number
US04604390

Reaction notes

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