Water → 8-(3-Bromophenylamino)[1,3]dioxolo[4,5-g]quinoline-7-carbonitrile

HRID 612005

반응식

HRID 612005 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:20])=[C:16]([OH:19])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:21]#[N:22])[CH:5]=[CH:6][CH:7]=1.Br[CH2:24]Cl.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[CH:17]=[C:16]4[O:19][CH2:24][O:20][C:15]4=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[C:21]#[N:22])[CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6333BromochloromethaneHCID 10796Cesium carbonateHCID 1354028484-(3-Bromophenylamino)-6,7-dihydroxy-3-quinolinecarbonitrile

생성물 1

HCID 53288838-(3-Bromophenylamino)[1,3]dioxolo[4,5-g]quinoline-7-carbonitrile수율 42.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
111 °C

실험 절차

A mixture of 2.17 g (6.09 mmole) of 4-[(3-bromophenyl)amino]-6,7-dihydroxy-3-quinolinecarbonitrile, 0.59 ml (1.18 g; 9.14 mmole) of bromochloromethane and 2.98 g (9.14 mmole) of cesium carbonate in 20 ml of N,N-dimethylformamide was heated and stirred for 2 hours in an oil bath at 111° C. The reaction was poured into 75 ml of water and extracted with four 50 ml portions of methylene chloride. The combined methylene chloride extracts were washed with several portions of water. This solution was taken to an oil in vacuo and this was dissolved in ethyl acetate. This solution was washed repeatedly with water, then with brine. The solution was dried over anhydrous magnesium sulfate, and taken to a solid in vacuo to give 0.95 g of 8-[(3-bromophenyl)amino]-[1,3]-dioxolo[4,5-g]quinoline-7-carbonitrile, m.p. 201-205° C.: mass spectrum (electrospray, m/e): M+H 368.1, 370.1.

후처리

  1. temperaturewas heated
  2. extractionextracted with four 50 ml portions of methylene chloride
  3. washThe combined methylene chloride extracts were washed with several portions of water
  4. dissolutionthis was dissolved in ethyl acetate
  5. washThis solution was washed repeatedly with water
  6. dry with materialThe solution was dried over anhydrous magnesium sulfate

출처 및 근거

ORD 기록
ord-cdb09c24625442dba30f7c3bc7768128
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06002008

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