Reaktion #76518

ord-6934c6c2cfa74c5fbc8a66f04445a66c

Reaktionsgleichung

CCOC(=O)C(=O)N(C)c1c([N+](=O)[O-])ccc2c1CCCN2
product
CCOC(=O)C(=O)N(C)c1c([N+](=O)[O-])ccc2c1CCCN2
[Methyl(1,2,3,4-tetrahydro-6-nitro-5-quinolinyl)-amino]oxo-acetic acid ethyl ester
→
Cn1c(=O)c(=O)[nH]c2ccc3c(c21)CCCN3
title compound
Ausbeute 69.0%
Cn1c(=O)c(=O)[nH]c2ccc3c(c21)CCCN3
1,4,7,8,9,10-Hexahydro-1-methyl-pyrido-[3,2-f]-quinoxaline-2,3-dione
Ausbeute 69.0%

Edukte

CCOC(=O)C(=O)N(C)c1c([N+](=O)[O-])ccc2c1CCCN2
product
CCOC(=O)C(=O)N(C)c1c([N+](=O)[O-])ccc2c1CCCN2
[Methyl(1,2,3,4-tetrahydro-6-nitro-5-quinolinyl)-amino]oxo-acetic acid ethyl ester

Reagenzien

[Pd]
Pd/C

Lösungsmittel

CC(=O)O
acetic acid

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeAfter removing the catalyst
  2. 2
    Filtrationby filtration through a celite pad
  3. 3
    Sonstigethe filtrate was evaporated
  4. 4
    Waschenthe yellow solide was washed with diethyl ether
  5. 5
    Sonstigedried

Vorschrift

A solution of the product from Example 94 (1.1 g) in 100 mL of acetic acid was treated with 20% Pd/C (0.3 g) and shaken on a Parr apparatus under a hydrogen atmosphere (50 psi) for 15.5 hours. After removing the catalyst by filtration through a celite pad, the filtrate was evaporated and the yellow solide was washed with diethyl ether and dried to give the title compound (0.55 g, 69% yield) mp>285° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06703391B2uspto-grants-2004_03