Acetic Acid → HCID 23092655, compound

HRID 2235361Notes

Reaction equation

HRID 2235361 reaction equation
[CH2:1]([C:3]1([CH2:17][CH3:18])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-])=O)[CH:10]=2)[N:5]([CH3:15])[C:4]1=[O:16])[CH3:2].[C:19](O)(=[O:21])[CH3:20]>[Ni]>[CH2:1]([C:3]1([CH2:17][CH3:18])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:19](=[O:21])[CH3:20])[CH:10]=2)[N:5]([CH3:15])[C:4]1=[O:16])[CH3:2]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 23092667HCID 23092667, compound

Product 1

HCID 23092655HCID 23092655, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

3,3-Diethyl-1-methyl-5-nitro-1,3-dihydro-indol-2-one (9.3 g) is dissolved in acetic acid (100 ml) and subjected to a catalytic hydrogenation with Raney-nickel (1 g) at 3 bar. After completion of the hydrogenation the mixture is filtered and evaporated. The residue is treated with acetic anhydride (10 ml) for 3 h at RT. The mixture is concentrated in vacuo and purified by flash chromatography on silica gel eluting with light petroleum/EtOAc. After re-crystallization from diisopropyl ether the compound (7.1 g) is obtained as a white solid.

Workup

  1. filtrationAfter completion of the hydrogenation the mixture is filtered
  2. customevaporated
  3. additionThe residue is treated with acetic anhydride (10 ml) for 3 h at RT
  4. concentrationThe mixture is concentrated in vacuo
  5. custompurified by flash chromatography on silica gel eluting with light petroleum/EtOAc
  6. customAfter re-crystallization from diisopropyl ether the compound (7.1 g)
  7. customis obtained as a white solid

Sources & evidence

ORD record
ord-8028164d857d4e73be63efacdc283248
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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