5-(tert-Butyl)-3,3-dimethyl-6-nitrobenzofuran-2(3H)-one → 6-Amino-5-(tert-butyl)-3,3-dimethylbenzofuran-2(3H)-one

HRID 1617307

Reaktionsgleichung

Reaktionsgleichung von HRID 1617307
[C:1]([C:5]1[C:6]([N+:17]([O-])=O)=[CH:7][C:8]2[O:12][C:11](=[O:13])[C:10]([CH3:15])([CH3:14])[C:9]=2[CH:16]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[NH2:17][C:6]1[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:16][C:9]2[C:10]([CH3:15])([CH3:14])[C:11](=[O:13])[O:12][C:8]=2[CH:7]=1

Komponenten

4

Edukt 1

HCID 595441545-(tert-Butyl)-3,3-dimethyl-6-nitrobenzofuran-2(3H)-one

Produkt 1

HCID 595441486-Amino-5-(tert-butyl)-3,3-dimethylbenzofuran-2(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Palladium on carbon (wet; 5 wt %) was placed into a round bottomed flask under nitrogen flow. 5-tert-butyl-3,3-dimethyl-6-nitro-benzofuran-2-one (4.7 g, 17.85 mmol) was then added to the vessel. Methanol (120 mL) was then carefully charged to the vessel under nitrogen atmosphere. The vessel was then purged with N2, evacuated, then charged with hydrogen gas. The vessel was evacuated and re-charged with hydrogen gas, and then a continuous hydrogen gas stream was introduced. After completion, the reaction was filtered through Celite® and the cake was washed with MeOH (300 ml). The solvent was removed in vacuo and the product dried under high vacuum to give a white crystalline solid. 1H-NMR (400 MHZ, DMSO-d6) δ 7.05 (s, 1H); 6.48 (s, 1H); 5.02 (s, 2H, NH2); 1.34 (s, 6H); 1.30 (s, 9H)

Aufarbeitung

  1. customThe vessel was then purged with N2
  2. customevacuated
  3. additioncharged with hydrogen gas
  4. customThe vessel was evacuated
  5. additionre-charged with hydrogen gas
  6. additiona continuous hydrogen gas stream was introduced
  7. filtrationAfter completion, the reaction was filtered through Celite®
  8. washthe cake was washed with MeOH (300 ml)
  9. customThe solvent was removed in vacuo
  10. customthe product dried under high vacuum
  11. customto give a white crystalline solid

Quellen und Nachweise

ORD-Eintrag
ord-aca503567009420f9174d906d4ee576a
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765957B2

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