Acetic Acid → 2,3-dihydro-3-oxo-1H-isoindole-5-sulfonamide hydrochloride

HRID 2412932Notes

Reaction equation

HRID 2412932 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:25])[N:7](C3CCN(CC4C=CC=CC=4)CC3)[C:8]2=O)=[CH:4][C:3]=1[S:26]([NH2:29])(=[O:28])=[O:27].O=C1C2C(=CC=CC=2)C(=O)N1.C(O)(=O)C.C(OCC)(=O)C>CO.[Zn]>[ClH:1].[O:25]=[C:6]1[C:5]2[C:9](=[CH:10][CH:2]=[C:3]([S:26]([NH2:29])(=[O:27])=[O:28])[CH:4]=2)[CH2:8][NH:7]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6809PhthalimideHCID 8857Ethyl AcetateHCID 133706016-Chloro-2,3-dihydro-1,3-dioxo-2-[1-(phenylmethyl)-4-piperidinyl]-1H-isoindole-5-sulfonamide

Product 1

HCID 233124542,3-dihydro-3-oxo-1H-isoindole-5-sulfonamide hydrochloride

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Reduction of the above product (a) 1,3-dioxoisoindole (5.0 g., 0.0107 mole) with zinc and acetic acid according to the method of Example 1(c) and conversion of the free base (partially purified by trituration wih ethyl acetate) to the hydrochloride salt in methanol afforded 6-chloro-2-[1-[(4-chloro-phenyl)phenyl)methyl]-4-piperidinyl]-2,3-dihydro-3-oxo-1H-isoindole-5-sulfonamide hydrochloride as the sesquihydrate, m.p. 256°-260° (dec.).

Sources & evidence

ORD record
ord-686b75b0271b4c4898dedefb8b7f1e67
Source dataset
uspto-grants-1985_01
Patent number
US04495194

Reaction notes

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