Sulfuric Acid → 1-[3-(Aminomethyl)-4-chlorophenyl]ethan-1-one
Reaction equation
ClCCl.[C:4]([C:7]1[CH:8]=[CH:9][C:10]([Cl:18])=[C:11]([CH2:13][NH:14]C(=O)C)[CH:12]=1)(=[O:6])[CH3:5].S(=O)(=O)(O)O.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[NH2:14][CH2:13][C:11]1[CH:12]=[C:7]([C:4](=[O:6])[CH3:5])[CH:8]=[CH:9][C:10]=1[Cl:18]Participants
Conditions
- Temperature
- 50 °C
Procedure
To 199.8 kg of a dichloromethane solution of N-[(5-acetyl-2-chlorophenyl)methyl]acetamide obtained in Example 3-(B), 90 kg of water and 46 kg (0.45 kmoles) of 98% sulfuric acid were added. Dichloromethane was distilled off under normal pressure over 1.5 hours until the inner temperature reaches 100° C., followed by aging for 6 hours. After the completion of the reaction, the reaction solution was cooled to 50° C. over 20 minutes and 90 kg of water and 105 kg of toluene were added. After cooling, 212 kg of an aqueous 25% sodium hydroxide solution was added dropwise at 15 to 25° C. over 2.5 hours. After heating to 40° C. over 30 minutes, the organic layer was partitioned to obtain a toluene solution of 1-[3-(aminomethyl)-4-chlorophenyl]ethan-1-one.
Workup
- distillationDichloromethane was distilled off under normal pressure over 1.5 hours until the inner temperature
- customreaches 100° C.
- customAfter the completion of the reaction
- temperatureAfter cooling
- temperatureAfter heating to 40° C. over 30 minutes
- customthe organic layer was partitioned
Sources & evidence
- ORD record
- ord-5ab73d059a2a48738a1c4d1a8182bd91
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07326813B2
Reaction notes
Loading…