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

HRID 446147

Reaction equation

HRID 446147 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-a6e6f63b935b49498a456f4814c1e8f6
Source dataset
uspto-grants-2013_07
Patent number
US08476442B2

Linked notes

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