4-Methylmorpholine → 3-methylamino-N-(2-naphthalene-1-yl-ethyl)-4-nitrobenzamide

HRID 412703Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 412703
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([OH:8])=O.C1CN([P+](ON2N=N[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.O.O[C:50]1[C:58]2N=NNC=2C=[CH:52][CH:51]=1.C[N:60]1CCO[CH2:62][CH2:61]1>CN(C)C=O>[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([NH:60][CH2:61][CH2:62][C:35]1[C:34]2[C:33](=[CH:58][CH:50]=[CH:51][CH:52]=2)[CH:38]=[CH:37][CH:36]=1)=[O:8]

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 2724699PyBOPHCID 221846233-(Methylamino)-4-nitrobenzoic acidHCID 178526939HCID 178526939, Verbindung

Produkt 1

HCID 185378103-methylamino-N-(2-naphthalene-1-yl-ethyl)-4-nitrobenzamideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture comprising 3-methylamino-4-nitrobenzoic acid (13.0 g, 66.3 mmol), PyBOP (38.0 g, 73.0 mmol), hydroxybenztriazole hydrate (9.9 g, 73.0 mmol), dimethylformamide (100 mL) and N-methylmorpholine (18.3 mL) was stirred at room temperature for 15 minutes and then 2-naphthylene-1-ylethylamine (13.8 g, 66.3 mmol) was added. The mixture was stirred for an additional 30 minutes and concentrated in vacuo. The residue was portioned between water and ethyl acetate and the organic layer was washed with water, 0.1M aqueous hydrochloric acid, saturated aqueous sodium hydrogencarbonate and then saturated aqueous sodium chloride, dried (magnesium sulfate), filtered and concentrated in vacuo. The residue was purified by recrystallization from hot ethanol to give 3-methylamino—N-(2-naphthalene-1-yl-ethyl)-4-nitrobenzamide as a bright red crystalline solid (21.3 g, 92% yield); 1H-NMR (300 MHz, DMSO-d6): 8.8 (t), 8.3 (d), 8.2 (q), 8.1 (d), 7.9 (d), 7.8 (d), 7.6-7.3 (m), 7.2 (s), 7.0 (d), 3.6 (q), 3.3 (t), 3.0 (d).

Aufarbeitung

  1. addition2-naphthylene-1-ylethylamine (13.8 g, 66.3 mmol) was added
  2. concentrationconcentrated in vacuo
  3. washthe organic layer was washed with water, 0.1M aqueous hydrochloric acid, saturated aqueous sodium hydrogencarbonate
  4. dry with materialsaturated aqueous sodium chloride, dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by recrystallization from hot ethanol

Quellen und Nachweise

ORD-Eintrag
ord-1f337f29dc994a19a6d69be49d7b241b
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562854B2

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