Water → 2-[2-(2-Methyl-1-oxopropyl)-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)dione

HRID 327842

Reaction equation

HRID 327842 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[Sn](Cl)(Cl)(Cl)Cl.[N:12]1([N:17]2[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]2=[O:27])[CH:16]=[CH:15][CH:14]=[CH:13]1.O>C(Cl)Cl>[CH3:3][CH:2]([CH3:4])[C:1]([C:13]1[N:12]([N:17]2[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]2=[O:27])[CH:16]=[CH:15][CH:14]=1)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24287Tin tetrachlorideHCID 62325Isobutyryl chlorideHCID 8537192-(1H-Pyrrol-1-yl)isoindoline-1,3-dione

Product 1

HCID 199732002-[2-(2-Methyl-1-oxopropyl)-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of isobutyryl chloride (5.4 ml) in DCM (250 ml) was added tin (IV) chloride (5.8 ml) at -10° C. under nitrogen. After stirring for 15 minutes in the cooling bath, 2-(1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione (10.0 g) was added portion-wise. The reaction mixture was allowed to warm to room temperature, and stir for three days, at which time it was poured into cold water. The layers were separated and the organic phase was washed twice with water, once with 5% HCl (aq.), and subsequently dried (MgSO4). Filtration and concentration gave the crude product. Purification via preparative HPLC (silica gel, DCM) afforded 2.5 g of the product as a solid, m.p. 147°-149° C.

Workup

  1. additionwas added portion-wise
  2. customThe layers were separated
  3. washthe organic phase was washed twice with water, once with 5% HCl (aq.)
  4. dry with materialsubsequently dried (MgSO4)
  5. filtrationFiltration and concentration
  6. customgave the crude product
  7. customPurification via preparative HPLC (silica gel, DCM)

Sources & evidence

ORD record
ord-4596beb64d1d4249969e62ff0627142b
Source dataset
uspto-grants-1993_12
Patent number
US05274116

Linked notes

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