Ammonium Hydroxide → Methyl 3-[3-(2-methyl-4,5-dihydro-1H-imidazol-1-yl)phenyl]isonicotinate

HRID 31395

반응식

HRID 31395 반응식
Cl[CH2:2][CH2:3][NH:4][C:5](=O)[CH3:6].P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:30]=[N:29][CH:28]=[CH:27][C:22]=2[C:23]([O:25][CH3:26])=[O:24])[CH:18]=[CH:19][CH:20]=1.[OH-].[NH4+]>C(OCC)(=O)C.ClCCl>[CH3:6][C:5]1[N:14]([C:15]2[CH:16]=[C:17]([C:21]3[CH:30]=[N:29][CH:28]=[CH:27][C:22]=3[C:23]([O:25][CH3:26])=[O:24])[CH:18]=[CH:19][CH:20]=2)[CH2:2][CH2:3][N:4]=1

참가 물질

7

반응물 4

HCID 14923Ammonium HydroxideHCID 24819Phosphorus pentachlorideHCID 81815N-(2-Chloroethyl)acetamideHCID 11368161Methyl 3-(3-aminophenyl)isonicotinate

생성물 1

HCID 11449306Methyl 3-[3-(2-methyl-4,5-dihydro-1H-imidazol-1-yl)phenyl]isonicotinate수율 48.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매2회

반응 조건

온도
0 °C

실험 절차

N-(2-chloroethyl)acetamide (0.32 g) in ethyl acetate (5 ml) was added over 10 min. to a stirred suspension of phosphorus pentachloride (0.55 g) in ethyl acetate (2 ml) at 0° C. under nitrogen to give a clear pale straw solution. After 45 min. at 0° C. a solution of methyl 3-(3-aminophenyl)isonicotinate (0.4 g) in dichloromethane (10 ml) was added over 15 min. at 0-5° C. The mixture was stirred at 0° C. for 10 min. and then allowed to warm up to 20° C. After 3 h the mixture was treated with ammonium hydroxide solution (28%, 5 ml) over 10 min. and stirring continued for ca. 1 h. The layers were allowed to separate, the organic layer was collected, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (dichloromethane:methanol:ammonia=100:10:1, v/v/v) to give 0.25 g (48%) of yellow oil.

후처리

  1. customto give a clear pale straw solution
  2. temperatureto warm up to 20° C
  3. stirringstirring
  4. waitcontinued for ca. 1 h
  5. customto separate
  6. customthe organic layer was collected
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (dichloromethane:methanol:ammonia=100:10:1, v/v/v)

출처 및 근거

ORD 기록
ord-507e9c0a8a6647cfa5a69d6b4dee8230
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425639B2

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