Hydrochloric Acid → 4-(2-Diethylaminoethoxy)-3-methoxyphenylamine

HRID 898523Notes

Reaction equation

HRID 898523 reaction equation
[CH2:1]([N:3]([CH2:18][CH3:19])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[O:16][CH3:17])[CH3:2].Cl.C(=O)([O-])[O-].[Na+].[Na+]>CCO.[Fe]>[CH2:18]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[O:16][CH3:17])[CH3:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 68878266Diethyl-[2-(2-methoxy-4-nitro-phenoxy)-ethyl]-amine

Product 1

HCID 224961344-(2-Diethylaminoethoxy)-3-methoxyphenylamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

0.77 g (2.87 mmol) of diethyl-[2-(2-methoxy-4-nitro-phenoxy)-ethyl]-amine was added to a suspension of 1.00 g (17.9 mmol) of iron powder in 7 mL EtOH and the mixture was stirred for 10 minutes at RT. 6.6 mL of conc. aqueous HCl was added dropwise within 15 minutes and the mixture was stirred for 1 hour. 100 ml of 2 M sodium carbonate solution was added and the mixture was exhaustively extracted with EtOAc. The combined org. extracts were dried over magnesium sulphate and evaporated down i. vac.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. extractionthe mixture was exhaustively extracted with EtOAc
  3. dry with materialextracts were dried over magnesium sulphate
  4. customevaporated down i

Sources & evidence

ORD record
ord-1e8b77f699af481ea186926f2ef04dc9
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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