Benzenesulfonyl chloride → 1-(Phenylsulfonyl)-3,4-dihydropyrrolo[4,3,2-de]isoquinolin-5(1H)-one

HRID 1096482Notes

Reaction equation

HRID 1096482 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[NH:13]1[C:23]2[C:24]3[C:15]([CH2:16][NH:17][C:18](=[O:25])[C:19]=3[CH:20]=[CH:21][CH:22]=2)=[CH:14]1>C(Cl)Cl>[C:1]1([S:7]([N:13]2[C:23]3[C:24]4[C:15]([CH2:16][NH:17][C:18](=[O:25])[C:19]=4[CH:20]=[CH:21][CH:22]=3)=[CH:14]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 3041095Pyrrolo(4,3,2-de)isoquinolin-5(1H)-one, 3,4-dihydro-

Product 1

HCID 667864451-(Phenylsulfonyl)-3,4-dihydropyrrolo[4,3,2-de]isoquinolin-5(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzenesulfonyl chloride (140 mg, 0.79 mmol), NBu4HSO4 (24 mg, 0.07 mmol) and 4M aq. NaOH (2 mL) were, in that order, added to 3,4-Dihydropyrrolo[4,3,2-de]isoquinolin-5(1H)-one, Intermediate 1 (124 mg, 0.72 mmol) in DCM (10 mL). The reaction was stirred at room temperature for 2 h and then extracted with water and DCM (×2). The product seems to be only partially soluble in DCM and some solid material in the water layer was filtered off and added to the DCM layer, which was concentrated and dried to give 227 mg of the title compound, as a light brown solid. MS m/z 313 [M+H]+.

Workup

  1. extractionextracted with water and DCM (×2)
  2. filtrationsome solid material in the water layer was filtered off
  3. additionadded to the DCM layer, which
  4. concentrationwas concentrated
  5. customdried

Sources & evidence

ORD record
ord-db9d809e872d431db45e31d856825443
Source dataset
uspto-grants-2012_03
Patent number
US08138333B2

Reaction notes

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