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Hydrochloric Acid → N-[3-[5-(4-Chlorophenyl)-1-(4-methoxyphenyl)-3-pyrazolyl]-propyl]hydroxyl-amine

HRID 1761572
ノート
印刷プレビュー

反応式

HRID 1761572 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:21][CH2:22][CH:23]=[N:24][OH:25])[CH:9]=2)=[CH:4][CH:3]=1.CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C.[BH3-]C#N.[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:21][CH2:22][CH2:23][NH:24][OH:25])[CH:9]=2)=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 5003444Sodium cyanoborohydrideHCID 54403492HCID 54403492、化合物

生成物 1

HCID 14497546N-[3-[5-(4-Chlorophenyl)-1-(4-methoxyphenyl)-3-pyrazolyl]-propyl]hydroxyl-amine

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒
2 回

実験手順

To a solution of the oxime 26 (2.70 g, 7.59 mM) in MeOH (50 ml), containing methyl orange (2 mg) as as indicator, was added a solution of NaBH3CN (0.52 g, 8.4 mM) in MeOH (20 ml), and a solution of 2N HCl, simultaneously, at such a rate to maintain a pH of 3 to 4. The reaction was stirred for 3 hours at room temperature, acidified to pH 1 and concentrated in vacuo. The residue was diluted with H2O (100 ml), adjusted to pH 8.5 with 5N NaOH, and extracted with EtOAc. The extracts were combined, dried (Na2SO4), filtered and concentrated in vacuo. The residue was chromatographed on Merck Silica Gel 60 (90 g, 230-400 mesh) with EtOAc:MeOH (9:1) as eluent. Crystallization from Et2O afforded pure 38 (1.64 g, 60%) as a white solid, mp=91°-93°. MS, m/e 357(M+).

後処理

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with H2O (100 ml)
  3. extractionextracted with EtOAc
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on Merck Silica Gel 60 (90 g, 230-400 mesh) with EtOAc:MeOH (9:1) as eluent
  8. customCrystallization from Et2O afforded pure 38 (1.64 g, 60%) as a white solid, mp=91°-93°

出典と根拠

ORDレコード
ord-f724477a705d4aa7a36fab78976fd40d
出典データセット
uspto-grants-1989_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04826868

反応ノート

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