Sodium Iodide → 4-(2,4-Dichloro-5-methoxyanilino)-8-methoxy-7-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrile

HRID 2213807노트

반응식

HRID 2213807 반응식
[Cl:1][C:2]1[CH:30]=[C:29]([Cl:31])[C:28]([O:32][CH3:33])=[CH:27][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]3[CH:18]=[C:17]([O:19][CH2:20][CH2:21]Cl)[C:16]([O:23][CH3:24])=[CH:15][C:12]=3[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:25]#[N:26].[Cl:34][C:35]1[CH:63]=[C:62]([Cl:64])[C:61]([O:65][CH3:66])=[CH:60][C:36]=1[NH:37][C:38]1[C:47]2[C:42](=[CH:43][C:44]3[CH:51]=[C:50]([O:52][CH3:53])[C:49]([O:54][CH2:55][CH2:56]Cl)=[CH:48][C:45]=3[CH:46]=2)[N:41]=[CH:40][C:39]=1[C:58]#[N:59].[NH:67]1[CH2:72][CH2:71][O:70][CH2:69][CH2:68]1.[I-].[Na+]>COCCOC>[Cl:34][C:35]1[CH:63]=[C:62]([Cl:64])[C:61]([O:65][CH3:66])=[CH:60][C:36]=1[NH:37][C:38]1[C:47]2[C:42](=[CH:43][C:44]3[CH:51]=[C:50]([O:52][CH3:53])[C:49]([O:54][CH2:55][CH2:56][N:67]4[CH2:72][CH2:71][O:70][CH2:69][CH2:68]4)=[CH:48][C:45]=3[CH:46]=2)[N:41]=[CH:40][C:39]=1[C:58]#[N:59].[Cl:1][C:2]1[CH:30]=[C:29]([Cl:31])[C:28]([O:32][CH3:33])=[CH:27][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]3[CH:18]=[C:17]([O:19][CH2:20][CH2:21][N:67]4[CH2:72][CH2:71][O:70][CH2:69][CH2:68]4)[C:16]([O:23][CH3:24])=[CH:15][C:12]=3[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:25]#[N:26]

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 8083MorpholineHCID 115696394-(2,4-Dichloro-5-methoxyanilino)-7-methoxy-8-(chloroethoxy)benzo[g]quinoline-3-carbonitrileHCID 116633894-(2,4-Dichloro-5-methoxyanilino)-8-methoxy-7-(chloroethoxy)benzo[g]quinoline-3-carbonitrile

생성물 2

HCID 53304284-(2,4-Dichloro-5-methoxyanilino)-8-methoxy-7-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrileHCID 53304374-(2,4-Dichloro-5-methoxyanilino)-7-methoxy-8-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrile

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
90 °C

실험 절차

A mixture of 0.436 g (0.87 mmol) of 4-(2,4-dichloro-5-methoxyanilino)-7-methoxy-8-(chloroethoxy)benzo[g]quinoline-3-carbonitrile and 4-(2,4-dichloro-5-methoxyanilino)-8-methoxy-7-(chloroethoxy)benzo[g]quinoline-3-carbonitrile (1:1 mixture), 2.0 mL (23.0 mmol) of morpholine and 0.05 g of sodium iodide in 2.0 mL of ethylene glycol dimethyl ether is heated at 90° C. for 3.5 hours under nitrogen. The mixture is cooled, solvent is removed in vacuo and the resulting residue is stirred with a saturated solution of sodium bicarbonate. The crude solid is collected by filtration, washed with water, and dried in vacuo. Purification is carried out by silica gel chromatography, eluting with a gradient of 97:3 to 90:10 ethyl acetate/methanol to yield 0.241 g of 4-(2,4-dichloro-5-methoxyanilino)-8-methoxy-7-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrile as a yellow solid, mp 210–212° C. and 0.203 g of 4-(2,4-dichloro-5-methoxyanilino)-7-methoxy-8-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrile as a yellow solid, mp 207–214° C.

후처리

  1. temperatureThe mixture is cooled
  2. customsolvent is removed in vacuo
  3. filtrationThe crude solid is collected by filtration
  4. washwashed with water
  5. customdried in vacuo
  6. customPurification
  7. washeluting with a gradient of 97:3 to 90:10 ethyl acetate/methanol

출처 및 근거

ORD 기록
ord-18951a0f50b24c3598ba019173a93f6f
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07105531B2

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