Methanol → Methyl 4-(aminocarbonyl)-3-methylbenzoate

HRID 735727ノート

反応式

HRID 735727 の反応式
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.C(N(CC)CC)C.[CH3:19][OH:20].CN([CH:24]=[O:25])C>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[NH2:8][C:6]([C:5]1[CH:9]=[CH:10][C:2]([C:19]([O:25][CH3:24])=[O:20])=[CH:3][C:4]=1[CH3:11])=[O:7]

参加物

8

反応物 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 206167664-Bromo-2-methylbenzamide

生成物 1

HCID 20642852Methyl 4-(aminocarbonyl)-3-methylbenzoate収率 70%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

A mixture of 4-bromo-2-methylbenzamide (1.65 g, 7.75 mmol), triethylamine (2.17 ml, 15.5 mmol), palladium acetate (0.0873 g, 0.388 mmol), 1,1′-bis(diphenylphosphino)ferrocene (0.215 g, 0.388 mmol), methanol (5 ml) and DMF (15 ml) was stirred under a carbon monoxide atmosphere at 70° C. for 22 hrs. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, and dried (over anhydrous MgSO4). After concentration under reduced pressure, the obtained crystals were recrystallized from ethyl acetate to give the title compound (1.05 g, 70%) as a pale-brown needle.

後処理

  1. temperatureAfter cooling to room temperature
  2. washwashed with water and saturated brine
  3. dry with materialdried (over anhydrous MgSO4)
  4. concentrationAfter concentration under reduced pressure
  5. customthe obtained crystals were recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-ac2fb812649a459a83967540f6670c96
出典データセット
uspto-grants-2009_09
特許番号
US07592453B2

反応ノート

読み込み中…