Ammonia → Methyl (2E)-3-(4-amino-3-nitrophenyl)prop-2-enoate

HRID 1713934ノート

反応式

HRID 1713934 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[NH3:17]>CS(C)=O>[NH2:17][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15]

参加物

4

反応物 2

HCID 222AmmoniaHCID 28818827methyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate

生成物 1

HCID 70314200Methyl (2E)-3-(4-amino-3-nitrophenyl)prop-2-enoate収率 89%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of methyl (2E)-3-(4-chloro-3-nitrophenyl)acrylate (from Step 1, 1 eq) in DMSO (0.4 M) at 140° C., ammonia gas was bubbled through for 6 h. The reaction mixture was cooled to RT, degassed with nitrogen, and poured into ice cold water. The precipitate formed was filtered washed with cold water and dried under vacuo to afford the title compound (89%) as a solid. 1H-NMR (400 MHz; DMSO-d6, 300 K) δ 3.70, (s, 3H), 6.46 (d, J 16, 1H), 7.04 (d, J 8.8, 1H), 7.60 (d, J 16, 1H), 7.82-7.86 (m, 3H), 8.25 (s, 1H); MS (ES−) m/z 221 (M−H)−.

後処理

  1. customdegassed with nitrogen
  2. additionpoured into ice cold water
  3. customThe precipitate formed
  4. filtrationwas filtered
  5. washwashed with cold water
  6. customdried under vacuo

出典と根拠

ORDレコード
ord-001828ea21dc4f8aac82d7cabbf32822
出典データセット
uspto-grants-2010_09
特許番号
US07795250B2

反応ノート

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