HCID 71209249, Verbindung → Methyl 6-amino-5-formyl-2-methyl-4-(p-tolyl)nicotinate

HRID 1912530Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1912530
[NH2:1][C:2]1[C:11]([CH2:12][OH:13])=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:21])[N:3]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[NH2:1][C:2]1[C:11]([CH:12]=[O:13])=[C:10]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:21])[N:3]=1

Komponenten

4

Edukt 2

HCID 71209249HCID 71209249, VerbindungHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 86675739Methyl 6-amino-5-formyl-2-methyl-4-(p-tolyl)nicotinateAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A suspension of methyl 6-amino-5-(hydroxymethyl)-2-methyl-4-(p-tolyl)nicotinate (3.14 g, 10.97 mmol) in dichloromethane (DCM) (100 ml) was treated with PCC (2.84 g, 13.16 mmol) and stirred at rt for 1 day. The mixture was filtered through Celite™, washed with DCM, and concentrated. Purification with column chromatography (0-100% EtOAc/Hexane) afforded methyl 6-amino-5-formyl-2-methyl-4-(p-tolyl)nicotinate (2.45 g, 8.62 mmol, 79% yield) as yellow solid: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.60 (s, 1 H), 7.26-7.21 (m, 2 H), 7.19-7.13 (m, 2 H), 3.48 (s, 3 H), 2.49 (s, 3 H), 2.41 (s, 3 H); LCMS (m/z) ES+=285 (M+1).

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite™
  2. washwashed with DCM
  3. concentrationconcentrated
  4. customPurification with column chromatography (0-100% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-bf494cfe3ab346e3b7f33904f3ad9051
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609653B2

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