Hydrochloric Acid → 2-Chloro-3,4-dimethoxyphenethylamine

HRID 525843Notes

Reaction equation

HRID 525843 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:11][C:12]1[C:17]([O:18][CH3:19])=[C:16]([O:20][CH3:21])[CH:15]=[CH:14][C:13]=1/[CH:22]=[CH:23]/[N+:24]([O-])=O.Cl>O1CCCC1.O>[Cl:11][C:12]1[C:17]([O:18][CH3:19])=[C:16]([O:20][CH3:21])[CH:15]=[CH:14][C:13]=1[CH2:22][CH2:23][NH2:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 130518862-Chloro-3,4-dimethoxy-1-[(E)-2-nitroethenyl]benzeneHCID 21226445Aluminium lithium hydride

Product 1

HCID 30177522-Chloro-3,4-dimethoxyphenethylamineYield 55.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To tetrahydrofuran (THF) (60 mL) was added lithium aluminum hydride (1.822 g, 48.0 mmol) at 0° C. and aluminium chloride (6.40 g, 48.0 mmol) in tetrahydrofuran (THF) (80 mL) was added via syringe. The solution of (E)-2-chloro-3,4-dimethoxy-1-(2-nitrovinyl)benzene (5.85 g, 24 mmol) in tetrahydrofuran (THF) (100 mL) was added via addition funnel over 40 min. Stirred at rt for 16 h. Water (8 ml) was added dropwise followed by 5N hydrochloric acid (60 ml). The mixture was washed with ether (2×200 mL) and the aqueous phase was made basic with 6N sodium hydroxide. The aqueous layer was extracted with ether (3×200 mL). Dried over magnesium sulfate, evaporated to give 2-(2-chloro-3,4-dimethoxyphenyl)ethanamine (2.85 g, 13.21 mmol, 55.1% yield). LCMS (M+H)+: 216.0

Workup

  1. washThe mixture was washed with ether (2×200 mL)
  2. extractionThe aqueous layer was extracted with ether (3×200 mL)
  3. dry with materialDried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-c9d5e48c84464c898df367c108ef3b5b
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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