3,4-Diaminotoluene → 3-(5-Methyl-benzoimidazol-2-yl)-quinolin-2-one

HRID 1017706

Reaktionsgleichung

Reaktionsgleichung von HRID 1017706
[O:1]=[C:2]1[C:11]([C:12](O)=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[NH2:15][C:16]1[CH:17]=[C:18]([CH3:23])[CH:19]=[CH:20][C:21]=1[NH2:22]>>[CH3:23][C:18]1[CH:19]=[CH:20][C:21]2[N:22]=[C:12]([C:11]3[C:2](=[O:1])[NH:3][C:4]4[C:9]([CH:10]=3)=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:15][C:16]=2[CH:17]=1

Komponenten

3

Edukt 2

HCID 103323,4-DiaminotolueneHCID 3324882-Quinolone-3-carboxylic acid

Produkt 1

HCID 1358341383-(5-Methyl-benzoimidazol-2-yl)-quinolin-2-one

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

A suspension of 2-oxo-1,2-dihydro-quinoline-3-carboxylic acid 1-1 (500 mg, 2.64 mmol, 1 equiv) and 3,4-diaminotoluene (646 mg, 5.29 mmol, 2.00 equiv) in polyphosphoric acid (10 mL) was heated under argon at 200° C. for 2 h. The hot reaction mixture was poured over ice (200 g), and the resulting mixture was allowed to stand until all polyphosphoric acid had dissolved. The precipitate was filtered, washed with water (200 mL), and air dried. The olive-colored solid was partitioned between aqueous sodium bicarbonate solution (200 mL) and ethyl acetate (200 mL). The organic layer was dried over sodium sulfate and concentrated to give 1-3 as a yellow solid. 1H NMR (300 MHz, CDCl3) major hydrogen-bonded rotational isomer: δ 15.20 (br s, 1H), 14.30 (br s, 1H), 9.18 (s, 1H), 7.77 (br d, 1H, J=7.6 Hz), 7.61 (br d, 1H, J=7.5 Hz), 7.60 (br t, 1H, J=7.5 Hz), 7.37 (br s, 1H), 7.36 (br d, 1H, J=7.5 Hz), 7.32 (br t, 1H, J=7.6), 7.14 (br d, 1H, J=8.2 Hz), 2.52 (s, 3H); HRMS (electrospray FT/ICR) calcd for C17H14N3O [M+H]+ 276.1131, found 276.1132; TLC (40% EtOAc in hexane) Rf=0.10.

Aufarbeitung

  1. dissolutionhad dissolved
  2. filtrationThe precipitate was filtered
  3. washwashed with water (200 mL), and air
  4. customdried
  5. customThe olive-colored solid was partitioned between aqueous sodium bicarbonate solution (200 mL) and ethyl acetate (200 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8586d3a78eee458a8fdce1983cb962f7
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479512B1

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