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

HRID 130801ノート

反応式

HRID 130801 の反応式
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]

参加物

4

反応物 2

HCID 8857Ethyl Acetate2 回HCID 597302948-methoxy-3-methyl-2,3-dihydro-1H-3-benzazepin-2-one

生成物 1

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

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

反応条件

温度
25 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-400a6a342db94e568b66773a8b359beb
出典データセット
uspto-grants-2008_06
特許番号
US07381719B2

反応ノート

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