Acetonitrile → 8-(2-Chloroethoxy)-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

HRID 989357노트

반응식

HRID 989357 반응식
C([Li])CCC.[C:6](#[N:8])[CH3:7].[Cl:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[CH:19]=[C:18]([C:25]([O:27]CC)=O)[C:17](/[N:30]=[CH:31]/N(C)C)=[CH:16]2.ClCCOC1C=C2C(C=C(/N=C/N(C)C)C(C(OCC)=O)=C2)=CC=1OC>O1CCCC1>[Cl:9][CH2:10][CH2:11][O:12][C:13]1[C:22]([O:23][CH3:24])=[CH:21][C:20]2[CH:19]=[C:18]3[C:17](=[CH:16][C:15]=2[CH:14]=1)[NH:30][CH:31]=[C:7]([C:6]#[N:8])[C:25]3=[O:27]

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 178418339ButyllithiumHCID 178468532HCID 178468532, 화합물HCID 178468534HCID 178468534, 화합물

생성물 1

HCID 115372188-(2-Chloroethoxy)-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-78 °C

실험 절차

To 2.5 mL of dry tetrahydrofuran at −78° C. is added 1.8 mL of 2.5 M n-butyllithium (4.4 mmol). Then 0.24 mL of dry acetonitrile in 4.5 mL of dry tetrahydrofuran is added dropwise over 10 minutes. This is stirred and additional 15 minutes at −78° C., then the ethyl 6-(2-chloroethoxy)-3-{[(E)-(dimethylamino)methylidene]-amino}-7-methoxy-2-naphthoate and ethyl 7-(2-chloroethoxy)-3-{[(E)-(dimethylamino)methylidene]amino}-6-methoxy-2-naphthoate (1:1 mixture) is dissolved in 3 mL of tetrahydrofuran and added dropwise over 15 minutes. The reaction mixture is stirred for 30 minutes at −78° C., then quenched with 0.57 mL of glacial acetic acid, and warmed to room temperature. To the yellow mixture is added 10 mL of water. The solids are filtered, washed with water and dried to give 0.502 g of 8-(2-chloroethoxy)-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile and 7-(2-chloroethoxy)-8-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile (1:1 mixture) as a yellow green solid (76%), m.p. 260-73° C. dec.

후처리

  1. additionadded dropwise over 15 minutes
  2. stirringThe reaction mixture is stirred for 30 minutes at −78° C.
  3. customquenched with 0.57 mL of glacial acetic acid
  4. temperaturewarmed to room temperature
  5. additionTo the yellow mixture is added 10 mL of water
  6. filtrationThe solids are filtered
  7. washwashed with water
  8. customdried

출처 및 근거

ORD 기록
ord-fe68b54451314a209a90848340f916c0
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06638929B2

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