HCID 18180288、化合物 → HCID 18180285、化合物

HRID 1359021ノート

反応式

HRID 1359021 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N+:15]([O-])=O)[CH:6]=[C:7]([O:13][CH3:14])[C:8]=1[O:9][CH2:10][CH2:11][OH:12]>[Pd].C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([O:13][CH3:14])[C:8]=1[O:9][CH2:10][CH2:11][OH:12])[NH2:15]

参加物

4

反応物 1

HCID 18180288HCID 18180288、化合物

生成物 1

HCID 18180285HCID 18180285、化合物収率 92%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A slurry of potassium 2,6-dimethoxy-4-nitrophenolate [Collins, R. P. and Davis, M. J. Chem. Soc. (1961), 1986] (38 g, 160 mmol) in DMF (600 ml) was treated with 2-bromoethanol (25 ml, 353 mmol) and hexamethylphosphorus triamide (31 ml, 176 mmol) and the reaction heated at 115° for 6 h. After cooling, the reaction was poured onto 1M hydrochloric acid (1.5 l) and extracted with ethyl acetate (5×500 ml). The organics were washed with 1M sodium hydroxide (4×700 ml), brine (200 ml) and drfied (MgSO4). Concentration in vacuo gave 3,5-dimethoxy-4-(2-hydroxyethoxy)nitrobenzene as an off white solid (31 g) δH (CDCl3) 7.52 (2H, s), 4.21 (2H, t, J 2.9 Hz), 3.94 (3H, s), 3.76 (2H, m) and 2.94 (1H, br s). MS (ES+) 266 (MNa+, 50%), 244 (MH+, 100%). A mixture of this nitrobenzene (750 mg, 3.16 mmol) and 10% palladium on carbon (75 mg) in ethanol (50 ml) was degassed and then subjected to an atmosphere of hydrogen (balloon) for 16 h. at 200. Dichloromethane was added and the solution filtered and solvent removed in vacuo to give 3,5-dimethoxy-4-(2-hydroxyethoxy)aniline as a grey solid (620 mg) after trituration with diethyl ether. δH (CDCl3+DMSO) 5.84 (2H, s), 3.87-3.84 (2H, m), 3.64 (6H, s) and 3.52-3.49 (2H, m). MS (ES+) 214 (MH+, 100%.

後処理

  1. customwas degassed
  2. additionDichloromethane was added
  3. filtrationthe solution filtered
  4. customsolvent removed in vacuo

出典と根拠

ORDレコード
ord-b77cf5ce684f4f8f9186d4a3a90fcc34
出典データセット
uspto-grants-2003_07
特許番号
US06599908B1

反応ノート

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