Sodium Hydroxide → 3-(2-Dimethylamino-ethoxy)-4-methylaniline

HRID 914963Notes

Reaction equation

HRID 914963 reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH:13]C(=O)OC(C)(C)C)[CH:9]=[CH:10][C:11]=1[CH3:12].[OH-].[Na+]>Cl>[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][C:11]=1[CH3:12])[NH2:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71166994tert-Butyl (3-(2-dimethylamino-ethoxy)-4-methyl-phenyl)-carbamate

Product 1

HCID 392392273-(2-Dimethylamino-ethoxy)-4-methylanilineYield 89.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 8 (1.15 g) in 6N HCl (10 mL) was heated at 60° C. for 4 hours. After cooling to room temperature, the solution was neutralized with 6N NaOH solution. The aqueous mixture was extracted with EtOAc (2×30 mL), the combined organic layers were washed with brine (1×50 mL) and dried over MgSO4. The solids were filtered, and the filtrate was concentrated under reduced pressure to give the desired product as an oil (0.68 g).

Workup

  1. extractionThe aqueous mixture was extracted with EtOAc (2×30 mL)
  2. washthe combined organic layers were washed with brine (1×50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationThe solids were filtered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-33783928e7394abaad2990d869dbd759
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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