HCID 67026916, compound → HCID 67026964, compound

HRID 1908783Notes

Reaction equation

HRID 1908783 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([CH:10]=[C:11]([CH3:13])[CH3:12])[C:7]([O:14][CH3:15])=[N:6][CH:5]=1>C(O)C>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([CH2:10][CH:11]([CH3:13])[CH3:12])[C:7]([O:14][CH3:15])=[N:6][CH:5]=1

Participants

3

Reactant 1

HCID 67026916HCID 67026916, compound

Product 1

HCID 67026964HCID 67026964, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 6-methoxy-5-(2-methyl-propenyl)-nicotinic acid methyl ester (300 mg, 1.36 mmol) in ethanol (5 mL) is added to a suspension of Pt(IV) oxide (40 mg) in ethanol (5 mL). The mixture is stirred under 1 atm of H2 at rt for 18 h. The catalyst is filtered off and the filtrate is concentrated. The crude product is purified on prep. TLC plates with heptane:EA 7:3 to give 5-isobutyl-6-methoxy-nicotinic acid methyl ester (260 mg) as a colourless oil; LC-MS: tR=1.08 min; [M+1]+=224.49.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated
  3. customThe crude product is purified on prep

Sources & evidence

ORD record
ord-b7d249c5ed5445c39b902cb770cfad7f
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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