Hydrochloric Acid → 3-Chloro-4-(2-diethylaminoethoxy)phenylamine

HRID 898515Notes

Reaction equation

HRID 898515 reaction equation
Cl.[Cl:2][C:3]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:4]=1[O:5][CH2:6][CH2:7][N:8]([CH2:11][CH3:12])[CH2:9][CH3:10].C(=O)(O)[O-].[Na+]>CCO.[Fe]>[Cl:2][C:3]1[CH:16]=[C:15]([NH2:17])[CH:14]=[CH:13][C:4]=1[O:5][CH2:6][CH2:7][N:8]([CH2:11][CH3:12])[CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68816504[2-(2-Chloro-4-nitro-phenoxy)-ethyl]-diethyl-amine

Product 1

HCID 167916763-Chloro-4-(2-diethylaminoethoxy)phenylamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 100 mL of conc. aqueous HCl in 100 mL EtOH was added dropwise to a suspension of 20.00 g (358 mmol) of iron powder and 20 g (73.33 mmol) of [2-(2-chloro-4-nitro-phenoxy)-ethyl]-diethyl-amine in 200 mL EtOH, while the temperature was kept below 20° C. by cooling with ice. The reaction mixture was stirred for 30 minutes, neutralised with 10% aqueous sodium bicarbonate solution and was exhaustively extracted with EtOAc. The combined org. extracts were dried over magnesium sulphate and evaporated down i. vac. The product was stored under a nitrogen atmosphere.

Workup

  1. customwas kept below 20° C.
  2. temperatureby cooling with ice
  3. extractionwas exhaustively extracted with EtOAc
  4. dry with materialextracts were dried over magnesium sulphate
  5. customevaporated down i

Sources & evidence

ORD record
ord-2735111ae98a468a84fef2a5526c20ae
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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