Sulfuric Acid → HCID 70872308, compound

HRID 1470154Notes

Reaction equation

HRID 1470154 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[CH2:4][NH:5][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.S(=O)(=O)(O)O>C(Cl)Cl>[Cl:22][C:20]1[CH:19]=[C:18]2[C:3](=[C:2]([Cl:1])[CH:21]=1)[CH2:4][NH:5][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

4

Reactant 2

HCID 1118Sulfuric AcidHCID 708721842-(2,4-Dichlorobenzylamino)-1-(3-nitrophenyl)ethanol2×

Product 1

HCID 70872308HCID 70872308, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

To 2-(2,4-dichlorobenzylamino)-1-(3-nitrophenyl)ethanol (intermediate 171.2) (500 mg, 1.47 mmol, 1.00 equiv) in DCM (10 mL) was added conc. sulfuric acid (4 mL) dropwise with stirring at 0-5° C. The resulting solution was stirred for 12 h at room temperature. The reaction was then quenched by the addition of water/ice. The pH value of the solution was adjusted to 10 with sodium hydroxide. The resulting solution was extracted with 2×50 mL of DCM and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 300 mg (63%) of 6,8-dichloro-4-(3-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline as yellow oil.

Workup

  1. stirringThe resulting solution was stirred for 12 h at room temperature
  2. customThe reaction was then quenched by the addition of water/ice
  3. extractionThe resulting solution was extracted with 2×50 mL of DCM
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThis resulted in 300 mg (63%) of 6,8-dichloro-4-(3-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline as yellow oil

Sources & evidence

ORD record
ord-b215afcf8f4f4a65b117e4a5c757473b
Source dataset
uspto-grants-2015_04
Patent number
US09006281B2

Reaction notes

Loading…