Methoxyacetyl chloride → 2-Methoxy-1-(3-nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone

HRID 1688044Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1688044
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=1)([O-:3])=[O:2].[CH3:15][O:16][CH2:17][C:18](Cl)=[O:19]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:15][O:16][CH2:17][C:18]([N:8]1[C:7]2[CH:13]=[CH:14][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[O:12][CH2:11][CH2:10][CH2:9]1)=[O:19]

Komponenten

5

Edukt 2

HCID 96623Methoxyacetyl chlorideHCID 672641803-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene

Produkt 1

HCID 672634692-Methoxy-1-(3-nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

3-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (203 mg, 1.04 mmol) and 4-Dimethylaminopyridine (13 mg, 0.10 mmol) in Pyridine (3.5 mL) was treated with Methoxyacetyl chloride (0.15 mL, 1.6 mmol) was added to the vial and stirred at rt. After 4 h, the mixture was partitioned between EtOAc and water, separated and the org. layer was washed with 1N HCl. After washing with brine and drying, 2-Methoxy-1-(3-nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone was isolated following silica gel chromatography (0-100% EtOAc:Hex) as yellow solids (270 mg, 97%). 1H-NMR (CDCl3): 7.96 (m, 2H), 7.36 (m, 1H), 4.82 (m, 1H), 4.25 (m, 2H), 3.89 (m, 3H), 3.34 (s, 3H), 2.96 (m, 1H), 2.13 (m, 2H).

Aufarbeitung

  1. additionwas added to the vial and
  2. customthe mixture was partitioned between EtOAc and water
  3. customseparated
  4. washlayer was washed with 1N HCl
  5. washAfter washing with brine
  6. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-b7cf21df92d14c05852ecc428be1f21f
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148391B2

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