Hydrochloric Acid → HCID 18180288, 화합물

HRID 1359020노트

반응식

HRID 1359020 반응식
[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]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 108982-BromoethanolHCID 15355Hexamethylphosphorous triamideHCID 22326798HCID 22326798, 화합물

생성물 1

HCID 18180288HCID 18180288, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-1545bf1d11c349b4897918c69e7b4ce8
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599908B1

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