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4-(2-(2-(2-(2-(5-Cyano-2-(2-methoxyethoxy)-4-nitrophenoxy)ethoxy)ethoxy)ethoxy)ethoxy)-5-(2-methoxyethoxy)-2-nitrobenzonitrile → 2-Amino-5-(2-(2-(2-(2-(5-amino-4-cyano-2-(2-methoxyethoxy)phenoxy)ethoxy)ethoxy)ethoxy)ethoxy)-4-(2-methoxyethoxy)benzonitrile

HRID 1405968
ノート
印刷プレビュー

反応式

HRID 1405968 の反応式
[C:1]([C:3]1[C:4]([N+:43]([O-])=O)=[CH:5][C:6]([O:38][CH2:39][CH2:40][O:41][CH3:42])=[C:7]([CH:37]=1)[O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][C:21]1[C:28]([O:29][CH2:30][CH2:31][O:32][CH3:33])=[CH:27][C:24]([C:25]#[N:26])=[C:23]([N+:34]([O-])=O)[CH:22]=1)#[N:2]>CC(O)=O.CC(O)C.[Fe]>[NH2:43][C:4]1[CH:5]=[C:6]([O:38][CH2:39][CH2:40][O:41][CH3:42])[C:7]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][C:21]2[CH:22]=[C:23]([NH2:34])[C:24]([C:25]#[N:26])=[CH:27][C:28]=2[O:29][CH2:30][CH2:31][O:32][CH3:33])=[CH:37][C:3]=1[C:1]#[N:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 1

HCID 867011944-(2-(2-(2-(2-(5-Cyano-2-(2-methoxyethoxy)-4-nitrophenoxy)ethoxy)ethoxy)ethoxy)ethoxy)-5-(2-methoxyethoxy)-2-nitrobenzonitrile

生成物 1

HCID 867011962-Amino-5-(2-(2-(2-(2-(5-amino-4-cyano-2-(2-methoxyethoxy)phenoxy)ethoxy)ethoxy)ethoxy)ethoxy)-4-(2-methoxyethoxy)benzonitrile収率 99.4%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 176Acetic Acid溶媒
HCID 3776
Isopropanol
溶媒

実験手順

To a solution of 4-(2-(2-(2-(2-(5-cyano-2-(2-methoxyethoxy)-4-nitrophenoxy)ethoxy)ethoxy)ethoxy)ethoxy)-5-(2-methoxyethoxy)-2-nitrobenzonitrile (0.2 g) in AcOH (10 mL) and i-PrOH (10 mL) was added iron powder (0.5 g). The resulting mixture was heated to reflux for 1 h. After reaction finished, the mixture was cooled to room temperature, filtered, the precipitate washed with EA (10 mL). The combined washings and filtrate were concentrated under reduced pressure and purification by silica chromatography to give 0.18 g of 2-amino-5-(2-(2-(2-(2-(5-amino-4-cyano-2-(2-methoxyethoxy)phenoxy)ethoxy)ethoxy)ethoxy)ethoxy)-4-(2-methoxyethoxy)benzonitrile. 1H-NMR (400 MHz, CDCl3): δ: 6.91 (s, 1H), 6.88 (s, 1H), 6.34 (s, 1H), 6.25 (s, 1H), 4.30 (br, 2H), 4.22-4.05 (m, 10H), 3.88-3.65 (m, 16H), 3.43 (s, 6H).

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 1 h
  3. customAfter reaction
  4. filtrationfiltered
  5. washthe precipitate washed with EA (10 mL)
  6. concentrationThe combined washings and filtrate were concentrated under reduced pressure and purification by silica chromatography

出典と根拠

ORDレコード
ord-d587fb63c2af4920b1209b00f1dfda96
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08916572B2

反応ノート

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