Methyl 2-methylindolizine-3-carboxylate → Methyl 2-methyl-1-nitrosoindolizine-3-carboxylate

HRID 502473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502473
[N:1]([O-:3])=O.[Na+].[CH3:5][C:6]1[CH:7]=[C:8]2[N:13]([C:14]=1[C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:11][CH:10]=[CH:9]2>O.C(O)(=O)C>[CH3:5][C:6]1[C:7]([N:1]=[O:3])=[C:8]2[N:13]([C:14]=1[C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:11][CH:10]=[CH:9]2

Komponenten

5

Edukt 2

HCID 13735249Methyl 2-methylindolizine-3-carboxylateHCID 23668193Sodium Nitrite

Produkt 1

HCID 57872297Methyl 2-methyl-1-nitrosoindolizine-3-carboxylateAusbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of sodium nitrite (2.2 g, 31.90 mmol) in water (10 mL) was added slowly at 0-5° C. to a stirred solution of methyl 2-methylindolizine-3-carboxylate 2 (3.9 g, 20.61 mmol) in glacial acetic acid (50 mL). After 30 min, the brown reaction mixture was poured into water. Green crystals were collected by filtration, washed with water and then dried under vacuum to give 3.7 g of expected compound; m.p.: 131-132° C. 1H NMR (CDCl3): 9.63 (d, J=7.0 Hz, 1H), 8.39 (d, J=8.5 Hz, 1H), 7.74-7.69 (m, 1H), 7.23-7.18 (m, 1H), 4.03 (s, 3H), 3.26 (s, 3H), 13C NMR (CDCl3): δ 162.5, 154.5, 141.7, 135.7, 127.9, 123.2, 118.4, 118.3, 114.5, 51.7, 11.1. Analysis calculated for C11H10N2O3: C, 60.55; H, 5.54; N, 12.84, found: C, 60.65; H, 5.60; N, 12.90.

Aufarbeitung

  1. filtrationGreen crystals were collected by filtration
  2. washwashed with water
  3. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-29429c4d0c6b431f8e812bf8458737fd
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776107B2

Notizen zur Reaktion

Wird geladen…