HCID 13591797, compound → HCID 22257136, compound

HRID 1611453Notes

Reaction equation

HRID 1611453 reaction equation
[C:1]([O:4][C:5]1[C:10]2[O:11][C:12]([CH3:15])([CH3:14])[CH2:13][C:9]=2[CH:8]=[C:7]([N+:16]([O-])=O)[CH:6]=1)(=[O:3])[CH3:2]>[Pd].C(O)C>[C:1]([O:4][C:5]1[C:10]2[O:11][C:12]([CH3:15])([CH3:14])[CH2:13][C:9]=2[CH:8]=[C:7]([NH2:16])[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 13591797HCID 13591797, compound

Product 1

HCID 22257136HCID 22257136, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3.5 grams (0.014 mole) of 2,2-dimethyl-5-nitro-2,3-dihydrobenzo[2,3-b]furan-7-yl acetate (known compound) and a catalytic amount of 10% palladium on carbon in 125 mL of ethanol was subjected to hydrogenation conditions using a Parr Hydrogenator. Upon completion of the uptake of the theoretical amount of hydrogen, the reaction mixture was filtered and concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using methylene chloride, followed by 5% methanol in methylene chloride as eluants. The appropriate fractions were combined and concentrated under reduced pressure, yielding 2.7 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. filtrationUpon completion of the uptake of the theoretical amount of hydrogen, the reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure to a residue
  3. customThe residue was purified with column chromatography on silica gel
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-caf04b7881cf4d4192c37435bb59c79c
Source dataset
uspto-grants-2006_01
Patent number
US06987194B2

Reaction notes

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