Reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[CH:9]([O:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16])([CH3:11])[CH3:10].C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:50](=[O:53])([O-])[O-].[Na+].[Na+].[C]=O>[Pd](Cl)Cl>[CH:9]([O:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH:16][C:50]([C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:53])([CH3:11])[CH3:10]Participants
Procedure
In an autoclave made of a metal were placed 12.7 g of ortho-chlorotoluene, 3 g of meta-isopropoxyaniline, 17.7 mg of palladium chloride, 426 mg of 1,4-bisdiphenylphosphinobutane and 23 g of sodium carbonate. The air in the autoclave was replaced with carbon monoxide introduced thereinto in several times, after which carbon monoxide was further introduced to adjust its pressure therein to 30 kg/cm2. The internal temperature was adjusted to 200° C. on a salt bath and the reaction was carried out thereon with stirring for 5 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and washed with water. Subsequently, the organic layer was separated, concentrated, and then recrystallized from ethyl acetatehexane to obtain 2.6 g of 3'-isopropoxy-2-toluanilide.
Workup
- additionintroduced
- customThe internal temperature was adjusted to 200° C. on a salt bath
- customAfter completion of the reaction
- washwashed with water
- customSubsequently, the organic layer was separated
- concentrationconcentrated
- customrecrystallized from ethyl acetatehexane
Sources & evidence
- ORD record
- ord-729a6d3dd161469c9dc4a35575be1157
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05296601
Linked notes
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