4-Methylmorpholine → 2-Amino-6-methoxybenzamide

HRID 591713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 591713
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4](O)=[O:5].CC[N:15]=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[NH4+].[OH-]>C1COCC1>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([NH2:15])=[O:5]

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27353572-Amino-6-methoxybenzoic Acid

Produkt 1

HCID 122648142-Amino-6-methoxybenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-amino-6-methoxy-benzoic acid (3.00 g, 17.9 mmol) in THF (90 mL), EDCl (7.89 g, 41.1 mmol) and HOBt (7.95 g, 51.9 mmol) were added and stirred at room temperature for 30 minutes then N-methylmorpholine (6.15 g, 60.0 mmol) and aqueous 50% v/v NH4OH (12 mL, 171.4 mmol) was added. The mixture was stirred for 16 hours at room temperature. The solvent was removed under reduced pressure and the residue was extracted with ethylacetate (4×100 mL), the combined organic phase was washed with water and brine, and dried over anhydrous sodium sulfate; the solvent was evaporated to give 2-amino-6-methoxy-benzamide as an off-white solid. Yield: 1.90 g, (65%).

Aufarbeitung

  1. stirringThe mixture was stirred for 16 hours at room temperature
  2. customThe solvent was removed under reduced pressure
  3. extractionthe residue was extracted with ethylacetate (4×100 mL)
  4. washthe combined organic phase was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-5433fdcfe75c4111bad2426fabcc7433
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238640B2

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