Chloral → 8-methyl-5-(4-chlorophenyl)-6,7,8,9-tetrahydro-1H-pyrrolo[3,2-h]isoquinoline-2,3-dione
Reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[C:7]2[C:12]=1[CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]2.[O:21]=[CH:22][C:23](Cl)(Cl)Cl.S([O-])([O-])(=O)=[O:28].[Na+].[Na+].Cl.NO>O>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C:6]2[C:7]3[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][C:12]=3[C:3]3[NH:2][C:22](=[O:21])[C:23](=[O:28])[C:4]=3[CH:5]=2)=[CH:19][CH:18]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 8-Amino-5-(4-chlorophenyl)-N-methyl-1,2,3,4-tetrahydroiso-quinoline hydrochloric acid salt (3.1 g, 10 mmol), chloral (1.5 ml, 15 mmol), sodium sulphate (14 g, 98.6 mmol), hydroxylamine hydrochloride (2.4 g, 15 mmol) and water (70 ml) was heated at reflux for 0.5 h. The mixture was allowed to reach room-temperature. The crystals were filtered and washed with water, followed by recrystallisation from ethanol (96%). The crystalline intermediate (2.0 g) was combined with methanesulphonic acid (20 ml) and heated for 15 min at 100° C. The crude mixture was poured out on ice and sodium hydroxide (25 ml, 10 M) was added. The crystalline product was recrystallized from ethanol (96%). Yield 0.54 g (29%). Mp decomp. 225° C.
Workup
- temperaturewas heated
- temperatureat reflux for 0.5 h
- filtrationThe crystals were filtered
- washwashed with water
- customfollowed by recrystallisation from ethanol (96%)
- additionThe crude mixture was poured out on ice and sodium hydroxide (25 ml, 10 M)
- additionwas added
- customThe crystalline product was recrystallized from ethanol (96%)
- custom225° C.
Sources & evidence
- ORD record
- ord-742032cfbf714991bea9c3feadd0d9aa
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07595336B2
Reaction notes
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