Hydrochloric Acid → HCID 18180288、化合物

HRID 1359020ノート

反応式

HRID 1359020 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([O:12][CH3:13])[C:4]=1[O-:14].[K+].Br[CH2:17][CH2:18][OH:19].CN(P(N(C)C)N(C)C)C.Cl>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([O:12][CH3:13])[C:4]=1[O:14][CH2:17][CH2:18][OH:19]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 108982-BromoethanolHCID 15355Hexamethylphosphorous triamideHCID 22326798HCID 22326798、化合物

生成物 1

HCID 18180288HCID 18180288、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide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. temperaturethe reaction heated at 115° for 6 h
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate (5×500 ml)
  4. washThe organics were washed with 1M sodium hydroxide (4×700 ml), brine (200 ml)
  5. concentrationConcentration in vacuo

出典と根拠

ORDレコード
ord-1545bf1d11c349b4897918c69e7b4ce8
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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