4-Methylmorpholine → 2-Amino-4-methoxybenzamide

HRID 591724

Reaktionsgleichung

Reaktionsgleichung von HRID 591724
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][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]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:15])=[O:5]

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 3510102-Amino-4-methoxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 140230022-Amino-4-methoxybenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-amino-4-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) were added. The mixture was stirred for 16 hours at room temperature. The solvent was removed under reduced pressure and the residue was extracted with ethyl acetate (4×100 mL). The combined organic phase was washed with water, then brine, and dried over anhydrous sodium sulfate. Solvent was evaporated to give 2-amino-4-methoxy-benzamide as an off-white solid. Yield: 1.80 g, (60%).

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 ethyl acetate (4×100 mL)
  4. washThe combined organic phase was washed with water
  5. dry with materialbrine, and dried over anhydrous sodium sulfate
  6. customSolvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-0b7fdd842aa14799a40de6ba58265e20
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238640B2

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