Triethylamine → HCID 178502672, compound

HRID 1690175Notes

Reaction equation

HRID 1690175 reaction equation
[OH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:11][O:12]CN.C1(N=C=[N:23][CH:24]2CCCCC2)CCCCC1.C(N(CC)CC)C>C(Cl)Cl.O>[CH3:11][O:12][N:23]([CH3:24])[C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[N:10][C:2]=1[OH:1]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 177781771-MethoxymethanamineHCID 178418543HCID 178418543, compound

Product 1

HCID 178502672HCID 178502672, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2-Hydroxynicotinic acid (2.00 g, 14.4 mmol) and methoxymethylamine (2.80 g, 28.8 mmol) were dissolved in methylene chloride (70 mL). The resultant mixture was added with dicyclohexylcarbodiimide (5.90 g, 28.8 mmol), triethylamine (4.00 mL), and 4-N,N-dimethylaminopyridine (176 mg, 1.44 mmol) at 0° C. The resultant mixture was stirred at room temperature overnight. Then the reaction solution was added with a small amount of water and concentrated in vacuo. Ethyl acetate was added and the generated crystal was filtered. Ethyl acetate was further added and the generated crystal was filtered in the same manner. The obtained residue was purified using silica-gel column chromatography (n-hexane/ethyl acetate=1/1) and N-methoxy-N-methyl-2-hydroxynicotinamide (2.18 g, yield 84%) was obtained as a colorless solid.

Workup

  1. concentrationconcentrated in vacuo
  2. additionEthyl acetate was added
  3. filtrationthe generated crystal was filtered
  4. additionEthyl acetate was further added
  5. filtrationthe generated crystal was filtered in the same manner
  6. customThe obtained residue was purified

Sources & evidence

ORD record
ord-64a84ce9b0fa45dc8471a62f12d9138e
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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