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

HRID 1009904노트

반응식

HRID 1009904 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

HCID 20642852Methyl 4-(aminocarbonyl)-3-methylbenzoate수율 70%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-31e577e194f64b99b794be0638f88165
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973163B2

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