HCID 70492998, compound → HCID 20255176, compound

HRID 638063Notes

Reaction equation

HRID 638063 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][CH:4]=[C:3]1[C:9]1[CH:40]=[CH:39][C:12]([O:13][CH2:14][CH:15]([OH:38])[CH2:16][NH:17][CH2:18][CH:19](CC2C=CC=CC=2)[O:20][C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([C:28](=[O:30])[NH2:29])[CH:22]=2)=[CH:11][CH:10]=1>CO.[Pd]>[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][CH:4]=[C:3]1[C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH:15]([OH:38])[CH2:16][NH:17][CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([C:28](=[O:30])[NH2:29])[CH:22]=2)=[CH:39][CH:40]=1

Participants

4

Reactant 1

HCID 70492998HCID 70492998, compound

Product 1

HCID 20255176HCID 20255176, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5.2 g of 1-[4-(1,6-dihydro-1-methyl-6-oxo-2-pyridyl)-phenoxy]-3-[2-(3-carbamoyl-4-hydroxyphenoxy)-N-benzylethylamino]-2-propanol in 100 ml of methanol is hydrogenated under normal conditions in the presence of 1 g of palladium-on-carbon catalyst (5%). The hydrogenated mixture is filtered with suction, the filtrate is concentrated to dryness by evaporation and the residue is washed with ethyl acetate. Recrystallisation from isopropanol yields pure 1-[4-(1,6-dihydro-1-methyl-6-oxo-2-pyridyl)-phenoxy]-3-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-2-propanol having a melting point of 148°-150°.

Workup

  1. filtrationThe hydrogenated mixture is filtered with suction
  2. concentrationthe filtrate is concentrated to dryness by evaporation
  3. washthe residue is washed with ethyl acetate
  4. customRecrystallisation from isopropanol

Sources & evidence

ORD record
ord-4e3591f2f83e4259a555ee452252188d
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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