Triethylamine → 3-Hydroxy-4-methoxy-4'-benzyloxypicolinanilide

HRID 350641

Reaction equation

HRID 350641 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.[OH:18][C:19]1[C:20]([C:27](O)=[O:28])=[N:21][CH:22]=[CH:23][C:24]=1[O:25][CH3:26].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl>C(Cl)(Cl)Cl>[OH:18][C:19]1[C:20]([C:27]([NH:14][C:13]2[CH:12]=[CH:11][C:10]([O:9][CH2:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[CH:16][CH:15]=2)=[O:28])=[N:21][CH:22]=[CH:23][C:24]=1[O:25][CH3:26]

Participants

7

Reactant 5

HCID 8471Triethylamine2×HCID 757711-HydroxybenzotriazoleHCID 27238314-Benzyloxyaniline hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 694976023-Hydroxy-4-methoxypicolinic acid hydrochloride

Product 1

HCID 155150083-Hydroxy-4-methoxy-4'-benzyloxypicolinanilideYield 59%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

4-Benzyloxyaniline hydrochloride (0.21 g, 0.87 mmol), 0.15 g (0.73 mmol) of 3-hydroxy-4-methoxypicolinic acid hydrochloride, 0.15 g (1.10 mmol) of 1-hydroxybenzotriazole, and 0.16 g (1.10 mmol) of triethylamine were mixed into chloroform to prepare a suspension (2 ml). A chloroform solution (2 ml) of WSCI.HCl (0.21 g, 1.10 mmol) and 0.11 g (1.10 mmol) of triethylamine were added dropwise at −20° C. to this suspension, and a reaction was then allowed to proceed at room temperature overnight. The reaction mixture was concentrated under the reduced pressure. The concentrate was redissolved in chloroform. The solution was washed with saturated brine, and was then dried over anhydrous sodium sulfate. The dried solution was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (chloroform) to give 0.15 g (yield 59%) of title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under the reduced pressure
  2. dissolutionThe concentrate was redissolved in chloroform
  3. washThe solution was washed with saturated brine
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. concentrationThe dried solution was concentrated under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (chloroform)

Sources & evidence

ORD record
ord-d133d006350943dbb74c6d34a66b4024
Source dataset
uspto-grants-2007_02
Patent number
US07183278B1

Linked notes

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