Methanol → 4-Amino-2-(2-diethylamino-ethoxy)-benzoic acid methyl ester

HRID 735813Notes

Reaction equation

HRID 735813 reaction equation
[CH2:1]([N:3]([CH2:14][CH3:15])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([NH2:13])[CH:10]=[CH:11][CH:12]=1)[CH3:2].C(N(CC)C[CH2:20][O:21][C:22]1C=CC=C([N+]([O-])=O)C=1)C.C[OH:34]>[Pd]>[CH3:22][O:21][C:20](=[O:34])[C:12]1[CH:11]=[CH:10][C:9]([NH2:13])=[CH:8][C:7]=1[O:6][CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 2996670HCID 2996670, compoundHCID 230087893-[2-(Diethylamino)ethoxy]aniline

Product 1

HCID 576328144-Amino-2-(2-diethylamino-ethoxy)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

3-(2-Diethylamino-ethoxy)-phenyl-amine can be prepared by the following procedure. In a Parr pressure bottle, a solution of diethyl-[2-(3-nitro-phenoxy)-ethyl]-amine (2.72 mmol) (from Example 11) in MeOH (10 mL) is added Pd (5% on carbon, 50% wet, 10% weight). The suspension is shaken at 40 psi of H2 for 2 h. The reaction is filtered through celite. The solvent is removed under reduced pressure to afford the title compound in quantitative yield. MS (m/z) (M+1)+ 267.1.

Workup

  1. filtrationThe reaction is filtered through celite
  2. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-8c6851e9dc424379ae5b117bdc7b55f8
Source dataset
uspto-grants-2009_09
Patent number
US07592349B2

Reaction notes

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