HCID 68474909, compound → HCID 68472086, compound

HRID 387661Notes

Reaction equation

HRID 387661 reaction equation
[H][H].[N+:3]([C:6]1[CH:7]=[C:8]([C:23]([O:25][CH3:26])=[O:24])[C:9]2[CH2:10][N:11]([CH:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[C:12](=[O:15])[C:13]=2[CH:14]=1)([O-])=O>CO.[Pd]>[NH2:3][C:6]1[CH:7]=[C:8]([C:23]([O:25][CH3:26])=[O:24])[C:9]2[CH2:10][N:11]([CH:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[C:12](=[O:15])[C:13]=2[CH:14]=1

Participants

5

Reactant 2

HCID 68474909HCID 68474909, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68472086HCID 68472086, compoundYield 75.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Conditions

Temperature
25 °C

Procedure

In an autoclave, 1.52 g of methyl 6-nitro-1-oxo-2-(1-propylbutyl)isoindoline-4-carboxylate are dissolved in 15 cm3 of methanol. 100 mg of 5% palladium-on-carbon in suspension in 1 cm3 of methanol are added. The autoclave is placed under 2 bar of hydrogen pressure and the mixture is stirred for 5 min at a temperature in the vicinity of 25° C. The reaction medium is filtered through a celite pellet. The celite is rinsed using 2×10 cm3 of methanol, then the organic phase is concentrated using a rotary evaporator under reduced pressure (5 kPa). The residual yellow oil is purified by column chromatography (silica 60 column—particle size 15-40 μm—150 g—eluent: 60% cyclohexane/40% ethyl acetate). The fractions are concentrated under reduced pressure (5 kPa). 1.05 g of methyl 6-amino-1-oxo-2-(1-propylbutyl)isoindoline-4-carboxylate are obtained in the form of a pale yellow solid.

Workup

  1. filtrationThe reaction medium is filtered through a celite pellet
  2. washThe celite is rinsed
  3. concentrationthe organic phase is concentrated
  4. customa rotary evaporator under reduced pressure (5 kPa)
  5. customThe residual yellow oil is purified by column chromatography (silica 60 column—particle size 15-40 μm—150 g—eluent: 60% cyclohexane/40% ethyl acetate)
  6. concentrationThe fractions are concentrated under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-1dda6dace759474f9a318d5fe0ba4c56
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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