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

HRID 612005

反応式

HRID 612005 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
111 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cdb09c24625442dba30f7c3bc7768128
出典データセット
uspto-grants-1999_12
特許番号
US06002008

関連ノート

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