Water → 7-Butyramido-2-methylquinoline-5,8-dione

HRID 1760199

反応式

HRID 1760199 の反応式
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].C(N[C:18]1[CH:27]=[C:26]([NH:28][C:29](=[O:33])[CH2:30][CH2:31][CH3:32])[C:25]([O:34]C(=O)CCC)=[C:24]2[C:19]=1[CH:20]=[CH:21][C:22]([CH3:40])=[N:23]2)(=O)CCC.[OH2:41]>C(O)(=O)C>[C:29]([NH:28][C:26]1[C:25](=[O:34])[C:24]2[N:23]=[C:22]([CH3:40])[CH:21]=[CH:20][C:19]=2[C:18](=[O:41])[CH:27]=1)(=[O:33])[CH2:30][CH2:31][CH3:32]

参加物

5

反応物 3

HCID 962WaterHCID 24502Potassium Dichromate2 回HCID 117739415,7-Dibutyramido-8-butyroxy-2-methylquinoline

生成物 1

HCID 111729337-Butyramido-2-methylquinoline-5,8-dione収率 77%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

This compound was prepared by the oxidation of the corresponding acylamido with potassium dichromate in glacial acetic acid. In a 500 ml. round-bottomed flask equipped with a magnetic bar, 5,7-dibutyramido-8-butyroxy-2-methylquinoline (34) (prepared as described in Examples 31-34) (3.29 g., 8.25 mmol) was suspended in 122 ml of glacial acetic acid. A solution of potassium dichromate (8.8 g., 0.03 mol) in 115 ml. of water was added and stirred. The stirred suspension began to dissolve but, after two hours, more solid continued to precipitate. Dichloromethane (70 ml.) was added to promote solution. The resulting two-phase solution mixture was stirred at room temperature overnight. The two-phase solution mixture was extracted with dichloromethane (12×50 ml.). The organic extracts were washed with a 3% sodium bicarbonate solution (200 ml.), dried with magnesium sulfate, and rotoevaporated to yield an orange-yellow solid. After vacuum drying, the solid weighed 1.65 g. (a yield of 77%). The product was recrystallized from ethyl acetate: mp. 188-189EC; 1H NMR (CDCl3) 1.00 (3H, t, J=7.4 Hz, C-7NHCOCH2CH2CH3), 1.69-1.82 (2H, m, C-7NHCOCH2CH2CH3), 2.48 (2H, t, J=7.4 Hz, C-7NHCOCH2CH2CH3), 2.74 (3H, s, C-2CH3), 7.53 (1H, d, J=8.0 Hz, C-3H), 7.90 (1H, s, C-6H), 8.28 (1H, d, J=8.0 Hz, C-4H), 8.36 (1H, br. s, C-7NH); IR (KBr) vmax 3338, 3275, 2964, 2935, 2875, 1711, 1682, 1654, 1644, 1615, 1588, 1502, 1323, 1310, 1133 cm−1; EIMS, m/e (relative intensity) 258 (81), 215 (7), 188 (base), 161 (66); HRMS, m/e for C14H14N2O3 calculated 258.100442, found 258.100227; analysis for C14H14N2O3 calculated C, 65.11; H, 5.46; N, 10.85; found C, 65.22; H. 5.51; N 10.01.

後処理

  1. customround-bottomed flask equipped with a magnetic bar
  2. dissolutionto dissolve but, after two hours
  3. customto precipitate
  4. additionDichloromethane (70 ml.) was added
  5. stirringThe resulting two-phase solution mixture was stirred at room temperature overnight
  6. extractionThe two-phase solution mixture was extracted with dichloromethane (12×50 ml.)
  7. washThe organic extracts were washed with a 3% sodium bicarbonate solution (200 ml.)
  8. dry with materialdried with magnesium sulfate
  9. customto yield an orange-yellow solid
  10. customAfter vacuum drying
  11. customThe product was recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-96eb5778104c4f069296d04f71cfa16a
出典データセット
uspto-grants-2005_01
特許番号
US06841555B2

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