Sodium Hydroxide → 6,8-Dichloro-2-methyl-4-(3-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline

HRID 45677Notes

Reaction equation

HRID 45677 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]([CH3:18])[CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)O.[OH-].[Na+]>ClCCl.S(=O)(=O)(O)O>[Cl:23][C:21]1[CH:20]=[C:19]2[C:3](=[C:2]([Cl:1])[CH:22]=1)[CH2:4][N:5]([CH3:18])[CH2:6][CH:7]2[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 674554962-((2,4-Dichlorobenzyl)(methyl)amino)-1-(3-nitrophenyl)ethanol

Product 1

HCID 674592816,8-Dichloro-2-methyl-4-(3-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Into a 500-mL 3-necked round-bottom flask, was placed a solution of 2-((2,4-dichlorobenzyl)(methyl)amino)-1-(3-nitrophenyl)ethanol (14 g, 39.55 mmol, 1.00 equiv) in dichloromethane (140 mL), sulfuric acid (140 mL). The resulting solution was stirred overnight at room temperature. The reaction progress was monitored by LCMS. The resulting solution was diluted with 100 mL of ice. The pH value of the solution was adjusted to 8-9 with sat. sodium hydroxide (100 mL). The resulting solution was extracted with 2×500 mL of ethyl acetate and the organic layers combined and dried over sodium sulfate. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10-1:5). This resulted in 7 g (51%) of 6,8-dichloro-2-methyl-4-(3-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline as a yellow solid.

Workup

  1. customInto a 500-mL 3-necked round-bottom flask, was placed
  2. extractionThe resulting solution was extracted with 2×500 mL of ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customThis resulted in 7 g (51%) of 6,8-dichloro-2-methyl-4-(3-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline as a yellow solid

Sources & evidence

ORD record
ord-41736b6e73a2488facea54ac2a62466d
Source dataset
uspto-grants-2013_09
Patent number
US08541448B2

Reaction notes

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