Sulfamic Acid → tert-Butyl 2-methyl-6-nitro-4-phenylquinoline-3-carboxylate

HRID 570377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 570377
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.NS(O)(=O)=O.[C:24]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:29])[CH2:25][C:26]([CH3:28])=O>CO.NS(O)(=O)=O>[CH3:28][C:26]1[C:25]([C:24]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]2[C:2](=[CH:15][CH:14]=[C:13]([N+:16]([O-:18])=[O:17])[CH:12]=2)[N:1]=1

Komponenten

6

Edukt 3

HCID 5987Sulfamic AcidHCID 15538Tert-butyl acetoacetateHCID 156812-Amino-5-nitrobenzophenone2×

Produkt 1

HCID 86713556tert-Butyl 2-methyl-6-nitro-4-phenylquinoline-3-carboxylateAusbeute 53,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5987Sulfamic AcidKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 2-amino-5-nitrobenzophenone (2 g, 8.26 mmol), H2NSO3H (0.09 g, 0.93 mmol) and tert-butyl acetoacetate (3 ml, 18 mmol) was stirred for 1 h at 120° C. under N2. To it, more of H2NSO3H (0.04 g, 0.41 mmol) was added and stirring was continued at 120° C. until all 2-amino-5-nitrobenzophenone was consumed (about 3 h). After cooling to room temperature the solid material formed was dispersed in MeOH (20 ml) and filtered off, washed with fresh MeOH and dried to give pure product as a creamy solid (1.6 g, 53%). 1H NMR (300 MHz, CDCl3) δ 8.41-8.5(m, 2H, 8.15 (d, J=9 Hz, 1H), 7.52-7.55(m, 3H), 7.3-7.4 (m, 2H), 2.82(s, 3H), 1.24(s, 9H).

Aufarbeitung

  1. stirringstirring
  2. customwas consumed (about 3 h)
  3. temperatureAfter cooling to room temperature the solid material
  4. customformed
  5. filtrationfiltered off
  6. washwashed with fresh MeOH
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-20a67c6075c647ed8e4b059ad666c9bb
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023848B2

Notizen zur Reaktion

Wird geladen…