HCID 20223681, compound → HCID 12397275, compound

HRID 1249621Notes

Reaction equation

HRID 1249621 reaction equation
[ClH:1].Cl.[OH:3][C:4]1[C:5]([CH2:19]O)=[N+:6]([O-])[C:7]([CH:10]([OH:17])[CH2:11][NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][CH:9]=1>[Pd].CO>[ClH:1].[ClH:1].[OH:3][C:4]1[C:5]([CH3:19])=[N:6][C:7]([CH:10]([OH:17])[CH2:11][NH:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 20223681HCID 20223681, compound

Product 1

HCID 12397275HCID 12397275, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into a 500 ml. Parr bottle there was introduced 13.4 g. (0.04 mole) of 3-hydroxy-6-(1-hydroxy-2-tertbutylaminoethyl)-2-hydroxymethylpyridine N-oxide dihydrochloride and 6.5 g. of 5% palladium on carbon catalyst in 150 ml. of methanol. Under a hydrogen pressure of 43 psi the mixture was shaken at room temperature for two days. The catalyst was removed by filtration under a nitrogen atmosphere followed by removal of the solvent in vacuo to give an oil which was triturated with isopropanol to induce crystallization. Filtration of the resulting solid afforded 3-hydroxy-6-(1-hydroxy-2-tert-butylaminoethyl)-2-methylpyridine dihydrochloride, 10.0 g. (85%) m.p. 226°-228.5° C. (dec.); NMR (DMSO d6)delta 7.80 (q, 2H, pyridyl H), 5.40 (br m, 1H); 3.30 (br m, 2H), 2.60 (s, 3H, 2--CH3) and 1.35 (s, 9H, t-Bn).

Workup

  1. additionParr bottle there was introduced 13.4 g
  2. customThe catalyst was removed by filtration under a nitrogen atmosphere
  3. customfollowed by removal of the solvent in vacuo
  4. customto give an oil which
  5. customwas triturated with isopropanol
  6. customcrystallization
  7. filtrationFiltration of the resulting solid

Sources & evidence

ORD record
ord-bff0a4efb22c40b78d2505da5da9595e
Source dataset
uspto-grants-1986_12
Patent number
US04632992

Reaction notes

Loading…