HCID 20442673, compound → HCID 12397272, compound

HRID 1632827Notes

Reaction equation

HRID 1632827 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:16]([OH:23])[CH2:17][NH:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N+:13]([O-])[CH:14]=1)C1C=CC=CC=1.OC1C=CC(C(NC(C)(C)C)C)=NC=1>[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH:16]([OH:23])[CH2:17][NH:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 20442673HCID 20442673, compoundHCID 70454632HCID 70454632, compound

Product 1

HCID 12397272HCID 12397272, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Into a 250 ml. Parr bottle there were introduced 250 mg. (0.79 mmole) of 5-benzyloxy-2-(1-hydroxy-2-tert-butylaminoethyl)pyridine N-oxide and 125 mg. of 5% palladium on carbon of 45 psi. The mixture was shaken at room temperature for 6 hours. The catalyst was removed by filtration under a nitrogen atmosphere followed by removel of the solvent in vacuo to give the product which was triturated with isopropanol and filtered. In this manner, there was obtained 175 mg. (75%) of 5-hydroxy-2-(1-tert-butylaminoethyl)pyridine as white crystals, m.p. 165°-168° C. (decomp).

Workup

  1. additionParr bottle there were introduced 250 mg
  2. customThe catalyst was removed by filtration under a nitrogen atmosphere
  3. customto give the product which
  4. customwas triturated with isopropanol
  5. filtrationfiltered
  6. customIn this manner, there was obtained 175 mg

Sources & evidence

ORD record
ord-aae45d0bc5a2418da4d30126b7b9706f
Source dataset
uspto-grants-1984_10
Patent number
US04477671

Reaction notes

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