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

HRID 1017706

反応式

HRID 1017706 の反応式
[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

参加物

3

反応物 2

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

生成物 1

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

反応条件

温度
200 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8586d3a78eee458a8fdce1983cb962f7
出典データセット
uspto-grants-2002_11
特許番号
US06479512B1

関連ノート

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