Ethyl Acetate → Methoxy-3-methyl-1,3,4,5-tetrahydrobenzo[d]azepin-2-one
Reaction equation
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]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
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).
Workup
- temperaturewhile maintaining a nitrogen blanket
- additionCharge the catalyst slurry to a 10-gallon autoclave
- washrinse the container with ethyl acetate (1 L)
- temperaturewhile maintaining a nitrogen
- custompurge
- customPurge the autoclave with nitrogen
- customseal the autoclave
- filtrationFilter the autoclave contents over hyflo
- washrinse with ethyl acetate
- concentrationconcentrate the filtrate
Sources & evidence
- ORD record
- ord-400a6a342db94e568b66773a8b359beb
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07381719B2
Reaction notes
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