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

HRID 263935

反応式

HRID 263935 の反応式
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].ClCC(N[C:17]1[CH:26]=[C:25]([NH:27][C:28](=[O:31])[CH2:29][Cl:30])[C:24]([OH:32])=[C:23]2[C:18]=1[CH:19]=[CH:20][C:21]([CH3:33])=[N:22]2)=O.[OH2:34]>C(O)(=O)C>[Cl:30][CH2:29][C:28]([NH:27][C:25]1[C:24](=[O:32])[C:23]2[N:22]=[C:21]([CH3:33])[CH:20]=[CH:19][C:18]=2[C:17](=[O:34])[CH:26]=1)=[O:31]

参加物

5

反応物 3

HCID 962WaterHCID 24502Potassium Dichromate2 回HCID 115374375,7-Bis(chloroacetamido)-8-hydroxy-2-methylquinoline

生成物 1

HCID 117016887-Chloroacetamido-2-methylquinoline-5,8-dione収率 59%

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-bottom flask equipped with a magnetic bar, 5,7-bis(chloroacetamido)-8-hydroxy-2-methylquinoline (32) (prepared as described in Example 32) (3.42 g., 0.01 mol) 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 the resulting dark solution was stirred at room temperature over-night. The solution was extracted with dichloromethane (12×50 ml.). The organic extracts were washed with 3% sodium bicarbonate solution (200 ml.), dried with magnesium sulfate, and rotoevaporated to yield a bright yellow solid. After vacuum drying, the nearly pure product weighed 1.56 g. (yield of 59%). The product was recrystallized from ethyl acetate: mp 196°-200° C. (dec.); 1H NMR (CDCl3) δ2.76 (3H, s, C-2CH3), 4.23 (2H, s, C-7NHCOCH2Cl), 7.56 (1H, d, J=8.1 Hz, C-3H), 7.89 (1H, s, C-6H), 8.30 (1H, d, J=8.1 Hz, C-4H), 9.48 (1H, br. s, C-7NH); IR (KBr) vmax 3299, 3078, 2948, 1712, 1683, 1641, 1614, 1588, 1515, 1398, 1384, 1323, 1130 cm-1 ; EIMS, m/e (relative intensity) 264/266 (M+, 2.9/1, 67) 229 (62), 215 (74), 201 (43), 188 (86), 161 (base), 132 (21); HRMS, m/e for C14H9ClN2O3, calculated 264.030170, found 264.029824; analysis for C14H9ClN2O3 calculated: C, 54.46; H, 3.43; Cl, 13.40; N, 10.58; found: C, 54.19; H, 3.37; C1, 13.29; N, 10.36.

後処理

  1. customround-bottom flask equipped with a magnetic bar
  2. extractionThe solution was extracted with dichloromethane (12×50 ml.)
  3. washThe organic extracts were washed with 3% sodium bicarbonate solution (200 ml.)
  4. dry with materialdried with magnesium sulfate
  5. customto yield a bright yellow solid
  6. customAfter vacuum drying
  7. customThe product was recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-f7ecded4a65a4eeda3298f8983ba9744
出典データセット
uspto-grants-1997_07
特許番号
US05646150

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