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

HRID 1278594

반응식

HRID 1278594 반응식
[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]

참가 물질

5

반응물 3

HCID 962WaterHCID 24502Potassium Dichromate2회HCID 117739415,7-Dibutyramido-8-butyroxy-2-methylquinoline

생성물 1

HCID 111729337-Butyramido-2-methylquinoline-5,8-dione수율 77%

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

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. 188-189 EC; 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 (1 H, 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.

후처리

  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

출처 및 근거

ORD 기록
ord-d6f26b9c01f5454e9d4fcf220bb0de72
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06444684B1

연결된 노트

불러오는 중…