Dimethylformamide → HCID 85867468, compound

HRID 730321Notes

Reaction equation

HRID 730321 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:17]([O-])=O)=[C:10]([S:13]([OH:16])(=[O:15])=[O:14])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].CN(C=O)C>CO.[Pd]>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH2:17])=[C:10]([S:13]([OH:16])(=[O:15])=[O:14])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 85867462HCID 85867462, compound2×

Product 1

HCID 85867468HCID 85867468, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A suspension of 1-acetyl-5-nitroindoline-6-sulfonic acid (Compound 2-3 in Scheme II) (9.0 g) in 250 mL of methanol was hydrogenated in the presence of 0.5 g of 10% Pd/C for 3 h. DMF (˜250 mL) was added to dissolve the precipitated product. The catalyst was removed by filtration through Celite® and the filtrate was concentrated to give a solid. The solid was suspended in methanol (50 mL), filtered and washed with small amount of methanol and ether. Drying under vacuum afforded 6.4 g of the desired amine as an off-white solid.

Workup

  1. dissolutionto dissolve the precipitated product
  2. customThe catalyst was removed by filtration through Celite®
  3. concentrationthe filtrate was concentrated
  4. customto give a solid
  5. filtrationfiltered
  6. washwashed with small amount of methanol and ether
  7. customDrying under vacuum

Sources & evidence

ORD record
ord-829e6461526b44ec9763f024d8444f9c
Source dataset
uspto-grants-2009_09
Patent number
US07582739B2

Reaction notes

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