Phosphorus oxychloride → 4-Chloro-7-methoxy-8-(2-chloroethoxy)benzo[g]quinoline-3-carbonitrile

HRID 989358ノート

反応式

HRID 989358 の反応式
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[C:21]([O:22][CH3:23])=[CH:20][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][C:7]=2[CH:6]=1)[NH:14][CH:13]=[C:12]([C:17]#[N:18])[C:11]3=O.[Cl:24]CCOC1C(OC)=CC2C=C3C(C(=O)C(C#N)=CN3)=CC=2C=1.P(Cl)(Cl)(Cl)=O>CN(C)C=O>[Cl:24][C:11]1[C:10]2[C:15](=[CH:16][C:7]3[CH:6]=[C:5]([O:4][CH2:3][CH2:2][Cl:1])[C:21]([O:22][CH3:23])=[CH:20][C:8]=3[CH:9]=2)[N:14]=[CH:13][C:12]=1[C:17]#[N:18]

参加物

5

反応物 3

HCID 24813Phosphorus oxychlorideHCID 115372188-(2-Chloroethoxy)-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrileHCID 116384657-(2-Chloroethoxy)-8-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

生成物 1

HCID 115157734-Chloro-7-methoxy-8-(2-chloroethoxy)benzo[g]quinoline-3-carbonitrile収率 87%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a slurry of 1.11 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) and 5 mL of phosphorus oxychloride is added 0.15 mL of anhydrous dimethylformamide. This is stirred and heated to reflux for 20 minutes using an oil bath, followed concentration in vacuo. The dark residue is quenched with 30 mL of cold water. The solid formed is collected, washed with water and dried to give 1.02 g (87%) of 4-chloro-7-methoxy-8(2-chloroethoxy)benzo[g]quinoline-3-carbonitrile and 4-chloro-8-methoxy-7(2-chloroethoxy)benzo[g]quinoline-3-carbonitrile (1:1 mixture) as a greenish yellow solid, m.p. 195-209° C. dec.

後処理

  1. temperatureheated
  2. temperatureto reflux for 20 minutes
  3. concentrationconcentration in vacuo
  4. customThe dark residue is quenched with 30 mL of cold water
  5. customThe solid formed
  6. customis collected
  7. washwashed with water
  8. customdried

出典と根拠

ORDレコード
ord-f4d69c700e514154887c632f90bab6da
出典データセット
uspto-grants-2003_10
特許番号
US06638929B2

反応ノート

読み込み中…