Perchloric Acid → 1-allyl-7-methyl-4-hydroxypyrido[2,3-b]pyridine-2(1H)-one-3-carboxylic acid

HRID 65687Notes

Reaction equation

HRID 65687 reaction equation
C([O:5][C:6]([C:8]1[C:18](=[O:19])[N:17]([CH2:20][CH:21]=[CH2:22])[C:11]2=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=[C:10]2[C:9]=1[OH:23])=[O:7])(C)(C)C.Cl(O)(=O)(=O)=O>C(#N)C>[CH2:20]([N:17]1[C:11]2=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=[C:10]2[C:9]([OH:23])=[C:8]([C:6]([OH:7])=[O:5])[C:18]1=[O:19])[CH:21]=[CH2:22]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 547352711-allyl-7-methyl-4-hydroxypyrido[2,3-b]pyridine-2(1H)-one-3-carboxylic acid t-butyl ester

Product 1

HCID 547171911-allyl-7-methyl-4-hydroxypyrido[2,3-b]pyridine-2(1H)-one-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2.0 grams of 1-allyl-7-methyl-4-hydroxypyrido[2,3-b]pyridine-2(1H)-one-3-carboxylic acid t-butyl ester in 25 ml. of acetonitrile is treated with 0.7 ml. of 60% aqueous perchloric acid at 0° C. The resulting precipitate is filtered off and washed with ether to obtain 1-allyl-7-methyl-4-hydroxypyrido[2,3-b]pyridine-2(1H)-one-3-carboxylic acid.

Workup

  1. customat 0° C
  2. filtrationThe resulting precipitate is filtered off
  3. washwashed with ether

Sources & evidence

ORD record
ord-db4c4ac15b6e412a953be1af21395afc
Source dataset
uspto-grants-1978_12
Patent number
US04128649

Reaction notes

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