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Chloral → 8-methyl-5-(4-chlorophenyl)-6,7,8,9-tetrahydro-1H-pyrrolo[3,2-h]isoquinoline-2,3-dione

HRID 736440
Notes
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Reaction equation

HRID 736440 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]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6407ChloralHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochlorideHCID 234358398-Amino-5-(4-chlorophenyl)-N-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloric acid salt

Product 1

HCID 543253028-methyl-5-(4-chlorophenyl)-6,7,8,9-tetrahydro-1H-pyrrolo[3,2-h]isoquinoline-2,3-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. temperaturewas heated
  2. temperatureat reflux for 0.5 h
  3. filtrationThe crystals were filtered
  4. washwashed with water
  5. customfollowed by recrystallisation from ethanol (96%)
  6. additionThe crude mixture was poured out on ice and sodium hydroxide (25 ml, 10 M)
  7. additionwas added
  8. customThe crystalline product was recrystallized from ethanol (96%)
  9. custom225° C.

Sources & evidence

ORD record
ord-742032cfbf714991bea9c3feadd0d9aa
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07595336B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes