2,6-Dichlorobenzaldehyde → 2-(2,6-Dichlorophenyl)imidazo[4,5-d]dipyrido[2,3-b:4',3'-f]azepin-3(8H)-ol

HRID 75202

反応式

HRID 75202 の反応式
[N:1]1[C:6]2[NH:7][C:8]3[CH:18]=[N:17][CH:16]=[CH:15][C:9]=3/[C:10](=[N:13]/[OH:14])/[C:11](=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+:23].[Cl:24][C:25]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:26]=1[CH:27]=O>C(O)(=O)C>[Cl:24][C:25]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:26]=1[C:27]1[N:13]([OH:14])[C:10]2[C:9]3[CH:15]=[CH:16][N:17]=[CH:18][C:8]=3[NH:7][C:6]3[N:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:11]=2[N:23]=1

参加物

5

反応物 3

HCID 67372,6-DichlorobenzaldehydeHCID 517165Ammonium AcetateHCID 178516816HCID 178516816、化合物

生成物 1

HCID 668867982-(2,6-Dichlorophenyl)imidazo[4,5-d]dipyrido[2,3-b:4',3'-f]azepin-3(8H)-ol収率 93.4%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

(6Z)-5H-dipyrido[2,3-b:4′,3′-f]azepine-5,6(11H)-dione 6-oxime (11.0 g, 0.0435 mol), ammonium acetate (50 g, 0.65 mol), 2,6-dichlorobenzaldehyde (15.2 g, 0.0870 mol) and acetic acid (200 mL) were heated at 90° C. for 30 minutes. The reaction was concentrated in vacuo to rigorously remove the acetic acid and then the residue was diluted with water (250 mL) and sodium bicarbonate saturated solution (250 mL) added to achieve a basic pH. Ethyl acetate (100 mL) and diethyl ether (300 mL) were then added. The desired product precipitated from the vigorously stirred mixture and was allowed to stand one hour prior to filtration that afforded the product as an off-yellow solid (16.1 g, 93%). This material was used without further purification in the next step. LCMS calculated for C19H12Cl2N5O (M+H)+: m/z=396. Elemental Analysis calculated for C19H13Cl4N5; C, 50.36; H, 2.89; Cl, 31.29; N, 15.45. Found: C, 48.93; H, 2.81; Cl, 30.57; N. 14.94.

後処理

  1. concentrationThe reaction was concentrated in vacuo
  2. customto rigorously remove the acetic acid
  3. additionthe residue was diluted with water (250 mL) and sodium bicarbonate saturated solution (250 mL)
  4. additionadded
  5. additionEthyl acetate (100 mL) and diethyl ether (300 mL) were then added
  6. customThe desired product precipitated from the vigorously stirred mixture
  7. filtrationto filtration

出典と根拠

ORDレコード
ord-51642fc19fdd4ffb9859dc9dcab0b7d1
出典データセット
uspto-grants-2014_09
特許番号
US08835423B2

関連ノート

読み込み中…