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3-[2-(Diethylamino)ethoxy]aniline → 4-Amino-2-(2-diethylamino-ethoxy)-benzoic acid methyl ester

HRID 2109799
Notes
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Reaction equation

HRID 2109799 reaction equation
C(N(CC)CCOC1C=C(N)C=CC=1)C.[CH3:16][O:17][C:18](=[O:48])[C:19]1[CH:24]=[CH:23][C:22]([NH:25]C2N=CC(C3C=CC(OC)=CC=3)=CN=2)=[CH:21][C:20]=1[O:40][CH2:41][CH2:42][N:43]([CH2:46][CH3:47])[CH2:44][CH3:45]>CO.[Pd]>[CH3:16][O:17][C:18](=[O:48])[C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][C:20]=1[O:40][CH2:41][CH2:42][N:43]([CH2:46][CH3:47])[CH2:44][CH3:45]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 230087893-[2-(Diethylamino)ethoxy]anilineHCID 576326182-(2-Diethylamino-ethoxy)-4-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-benzoic acid methyl ester

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

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 1i) 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-1d5dcd6cdcb5424f917109eba17706f7
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07514447B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes