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

HRID 378337

反応式

HRID 378337 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 overnight. 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 196-200EC (dec.); 1H NMR (CDCl3) * 2.76 (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; Cl, 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-f1f00564d4e54ed8abf5006437e567cd
出典データセット
uspto-grants-2000_02
特許番号
US06030983

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