2,4-Dichloro-5-methoxyaniline → 8-(2-Chloroethoxy)-4-(2,4-dichloro-5-methoxyanilino)-7-methoxybenzo[b][1,8]naphthyridine-3-carbonitrile

HRID 2213839

反応式

HRID 2213839 の反応式
Cl[C:2]1[C:3]2[CH:4]=[C:5]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH2:21][CH2:22][Cl:23])=[CH:14][C:6]3=[N:7][C:8]=2[N:9]=[CH:10][C:11]=1[C:12]#[N:13].[Cl:24][C:25]1[CH:31]=[C:30]([Cl:32])[C:29]([O:33][CH3:34])=[CH:28][C:26]=1[NH2:27]>C(OCCO)C>[Cl:23][CH2:22][CH2:21][O:20][C:15]1[C:16]([O:18][CH3:19])=[CH:17][C:5]2[C:6]([CH:14]=1)=[N:7][C:8]1[N:9]=[CH:10][C:11]([C:12]#[N:13])=[C:2]([NH:27][C:26]3[CH:28]=[C:29]([O:33][CH3:34])[C:30]([Cl:32])=[CH:31][C:25]=3[Cl:24])[C:3]=1[CH:4]=2

参加物

4

反応物 2

HCID 14766362,4-Dichloro-5-methoxyanilineHCID 219564934-Chloro-8-(2-chloroethoxy)-7-methoxybenzo[b][1,8]naphthyridine-3-carbonitrile

生成物 1

HCID 101641738-(2-Chloroethoxy)-4-(2,4-dichloro-5-methoxyanilino)-7-methoxybenzo[b][1,8]naphthyridine-3-carbonitrile収率 41.2%

試薬・触媒・溶媒 1

HCID 8076Glycol monoethyl ether溶媒

実験手順

A mixture of 4-chloro-8-(2-chloroethoxy)-7-methoxybenzo[b][1,8]naphthyridine-3-carbonitrile (500 mg, 1.43 mmol) and 2,4-dichloro-5-methoxyaniline (460 mg, 2.39 mmol) in 40 mL of 2-ethoxyethanol is heated at reflux for 20 minutes then cooled to room temperature. The solution is partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is partitioned between ethyl acetate and an aqueous solution of sodium hydroxide and sodium bicarbonate (pH 14). The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo. Ethyl acetate and diethyl ether are added to the residue and the resultant orange solid is collected by filtration to provide 297 mg (41%) of 8-(2-chloroethoxy)-4-(2,4-dichloro-5-methoxyanilino)-7-methoxybenzo[b][1,8]naphthyridine-3-carbonitrile, mp 227–230° C. dec.

後処理

  1. temperatureis heated
  2. temperatureat reflux for 20 minutes
  3. customThe solution is partitioned between ethyl acetate and saturated sodium bicarbonate
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is partitioned between ethyl acetate
  8. dry with materialThe organic layer is dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. additionEthyl acetate and diethyl ether are added to the residue
  12. filtrationthe resultant orange solid is collected by filtration

出典と根拠

ORDレコード
ord-10c402d58fed4610b51dc32aa028b976
出典データセット
uspto-grants-2006_09
特許番号
US07105531B2

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