1-Methylimidazole → Butyl 3-(3-(methylamino)-4-nitrophenyl)prop-2-enoate

HRID 1907891노트

반응식

HRID 1907891 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:11][CH3:12])[CH:3]=1.[Li+].[Cl-].CCN(C(C)C)C(C)C.[C:24]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])(=[O:27])[CH:25]=[CH2:26].CN1C=CN=C1>CC(N(C)C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:12][NH:11][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9])[CH:26]=[CH:25][C:24]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:27]

참가 물질

8

반응물 5

HCID 13901-MethylimidazoleHCID 8846Butyl AcrylateHCID 81531DiisopropylethylamineHCID 2580415-chloro-N-methyl-2-nitroanilineHCID 433294Lithium Chloride

생성물 1

HCID 66835685Butyl 3-(3-(methylamino)-4-nitrophenyl)prop-2-enoate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 31374Dimethylacetamide용매

반응 조건

온도
110 °C

실험 절차

To a mixture of 4-chloro-2-methylaminonitrobenzene (50.0 g, 268.0 mmol, 1.0 eq), Pd(OAc)2 (0.30 g, 1.3 mmol, 0.005 eq) and LiCl (11.4 g 268.0 mmol, 1.0 eq) in DMAc (250 mL) was added iPr2NEt (56 mL, 321.5 mmol, 1.2 eq) followed by n-butyl acrylate (40 mL, 281.4 mmol, 1.05 eq) under nitrogen. The reaction mixture was stirred at 110° C. for 12 h, then cooled to 50° C. 1-methylimidazole (10.6 mL, 134.0 mmol, 0.5 eq) was added and the mixture was stirred for 30 min before filtering and adding water (250 mL). The resulting mixture was cooled to r.t. over 1 h. The resulting solid was filtered and washed with water and dried to yield n-butyl 3-methylamino-4-nitrocinnamate (71.8 g, 96%, 99.2 A % purity).

후처리

  1. temperaturecooled to 50° C
  2. stirringthe mixture was stirred for 30 min
  3. filtrationbefore filtering
  4. additionadding water (250 mL)
  5. temperatureThe resulting mixture was cooled to r.t. over 1 h
  6. filtrationThe resulting solid was filtered
  7. washwashed with water
  8. customdried

출처 및 근거

ORD 기록
ord-d425e3b5424740d19c088e94c7ec6394
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598183B2

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