Acetic Acid → 1-Isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid

HRID 12312

Reaktionsgleichung

Reaktionsgleichung von HRID 12312
CC1(C)[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])O1.[CH:11]([NH:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=O)([CH3:13])[CH3:12].C(O)(=O)C.C(N)CN>CO>[CH:11]([N:14]1[C:15]2[C:16](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[C:5]([C:6]([OH:7])=[O:8])[C:4]1=[O:9])([CH3:13])[CH3:12]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 3301EthylenediamineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione2×HCID 110410352-((Propan-2-yl)amino)benzaldehyde

Produkt 1

HCID 109442901-Isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acidAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2,2-Dimethyl-[1,3]dioxane-4,6-dione, commonly Meldrum's acid, (166.9 g, 1.16 mol) was added to a stirred solution of 2-isopropylaminobenzaldehyde (105 g, 0.64 mol), acetic acid (73.6 mL, 1.29 mol) and ethylenediamine (43.0 mL, 0.64 mol) in methanol (1 L) at 0° C. The reaction mixture was stirred for 1 h at 0° C. and then at room temperature overnight. The resulting suspension was filtered and the solid washed with methanol and collected to yield the title intermediate, 1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (146 g, 98%) as an off-white solid. 1H NMR (CDCl3; 300 MHz): 1.72 (d, 6H, CH(CH3)2), 5.50 (bs, 1H, CH(CH3)2), 7.44 (t, 1H, ArH), 7.75-7.77 (m, 2H, ArH), 7.82 (d, 1H, ArH), 8.89 (s, 1H, CH).

Aufarbeitung

  1. customat room temperature
  2. customovernight
  3. filtrationThe resulting suspension was filtered
  4. washthe solid washed with methanol
  5. customcollected

Quellen und Nachweise

ORD-Eintrag
ord-9b73b2020f5846258bd4e50f40a5b179
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728004B2

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