2-Amino-4-methoxyphenol → HCID 66880059, compound

HRID 1913683Notes

Reaction equation

HRID 1913683 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[OH:10].Cl.[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1>N1C=CC=CC=1>[OH:10][C:3]1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=1[NH:1][C:12](=[O:19])[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 14191082-Amino-4-methoxyphenolHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 66880059HCID 66880059, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2.5 g of a crude product of 2-amino-4-methoxyphenol, 3.2 g of isonicotinic acid chloride hydrochloride and 20 ml of pyridine was heated to reflux for 12 hours. The reaction mixture was poured into ice water, and precipitated deposits are collected by filtration. The obtained solid was dissolved in ethyl acetate, washed with water and a saturated sodium chloride solution, and dried over magnesium sulfate. Activated carbon was added thereto, followed by filtration through Celite™. The filtrate was concentrated under reduced pressure to give N-(2-hydroxy-5-methoxyphenyl)isonicotinamide.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours
  3. customprecipitated deposits
  4. filtrationare collected by filtration
  5. dissolutionThe obtained solid was dissolved in ethyl acetate
  6. washwashed with water
  7. dry with materiala saturated sodium chloride solution, and dried over magnesium sulfate
  8. additionActivated carbon was added
  9. filtrationfollowed by filtration through Celite™
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-97355ca1d3b84f2cbcf6ddb7e2cd5a65
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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