Methyl 2-[3-vinyl-4-(quinolin-2-yl-methoxy)phenyl]acetate → Methyl 2-[3-ethyl-4-(quinolin-2-yl-methoxy)phenyl]acetate

HRID 1464392Notes

Reaction equation

HRID 1464392 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1)=[CH2:2]>CO.C(O)(=O)C.[Pd]>[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1)[CH3:2]

Participants

5

Reactant 1

HCID 19087790Methyl 2-[3-vinyl-4-(quinolin-2-yl-methoxy)phenyl]acetate

Product 1

HCID 19087796Methyl 2-[3-ethyl-4-(quinolin-2-yl-methoxy)phenyl]acetate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

14.3 g (0.0429 mol) of the compound from Example XXXII are dissolved in 150 ml of methanol and 15 ml of glacial acetic acid, 1.5 g of 5% strength Pd-C are added, and the reaction mixture is heated to 30°-35° C. and hydrogenated. It is filtered through silica gel, the filtrate is concentrated in vacuo and the residue is recrystallised from isopropanol.

Workup

  1. temperaturethe reaction mixture is heated to 30°-35° C.
  2. filtrationIt is filtered through silica gel
  3. concentrationthe filtrate is concentrated in vacuo
  4. customthe residue is recrystallised from isopropanol

Sources & evidence

ORD record
ord-0301438e11134b3a9e324cefb940d8fd
Source dataset
uspto-grants-1994_04
Patent number
US05304563

Reaction notes

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