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

HRID 1907891ノート

反応式

HRID 1907891 の反応式
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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d425e3b5424740d19c088e94c7ec6394
出典データセット
uspto-grants-2013_12
特許番号
US08598183B2

反応ノート

読み込み中…