Ethyl Acetate → Methoxy-3-methyl-1,3,4,5-tetrahydrobenzo[d]azepin-2-one

HRID 130801노트

반응식

HRID 130801 반응식
CO[C:3]1[CH:4]=[CH:5][C:6]2[CH:12]=[CH:11][N:10]([CH3:13])[C:9](=[O:14])[CH2:8][C:7]=2[CH:15]=1.[C:16](OCC)(=[O:18])C>[Pd]>[CH3:16][O:18][CH:8]1[C:7]2[CH:15]=[CH:3][CH:4]=[CH:5][C:6]=2[CH2:12][CH2:11][N:10]([CH3:13])[C:9]1=[O:14]

참가 물질

4

반응물 2

HCID 8857Ethyl Acetate2회HCID 597302948-methoxy-3-methyl-2,3-dihydro-1H-3-benzazepin-2-one

생성물 1

HCID 68749213Methoxy-3-methyl-1,3,4,5-tetrahydrobenzo[d]azepin-2-one수율 93%

시약·촉매·용매 1

HCID 23938Palladium촉매

반응 조건

온도
25 °C

실험 절차

Weigh out 5% Pd on carbon (100 g) to a suitable container and wet the catalyst with ethyl acetate (2 L) while maintaining a nitrogen blanket. Charge the catalyst slurry to a 10-gallon autoclave and rinse the container with ethyl acetate (1 L) while maintaining a nitrogen purge. Add 8-methoxy-3-methyl-1,3-dihydrobenzo[d]azepin-2-one (920 g, 4.5 mol) to the autoclave and rinse with ethyl acetate (4 L). Purge the autoclave with nitrogen, seal the autoclave and pressurize with hydrogen to 50 psi while stirring at 800 rpm and maintaining the reaction temperature between 20-30° C. The reaction is determined to be complete by 1H NMR after 5 hours. Filter the autoclave contents over hyflo and rinse with ethyl acetate, then concentrate the filtrate to obtain the product methoxy-3-methyl-1,3,4,5-tetrahydrobenzo[d]azepin-2-one as an off-white solid (868 g, 93% yield).

후처리

  1. temperaturewhile maintaining a nitrogen blanket
  2. additionCharge the catalyst slurry to a 10-gallon autoclave
  3. washrinse the container with ethyl acetate (1 L)
  4. temperaturewhile maintaining a nitrogen
  5. custompurge
  6. customPurge the autoclave with nitrogen
  7. customseal the autoclave
  8. filtrationFilter the autoclave contents over hyflo
  9. washrinse with ethyl acetate
  10. concentrationconcentrate the filtrate

출처 및 근거

ORD 기록
ord-400a6a342db94e568b66773a8b359beb
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381719B2

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