2-(2-Chloro-5-nitro-phenoxymethyl)-tetrahydrofuran → 4-Chloro-3-((tetrahydrofuran-2-yl)methoxy)benzenamine

HRID 491605Notes

Reaction equation

HRID 491605 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:3]=1[O:4][CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][O:7]1>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:3]=1[O:4][CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][O:7]1

Participants

4

Reactant 1

HCID 690160502-(2-Chloro-5-nitro-phenoxymethyl)-tetrahydrofuran

Product 1

HCID 640085904-Chloro-3-((tetrahydrofuran-2-yl)methoxy)benzenamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(2-chloro-5-nitro-phenoxymethyl)-tetrahydrofuran (0.45 g, 1.75 mmol) in EtOAc (10 mL) was degassed with argon then charged with 10% by weight Pd/C (0.4 g). The mixture was stirred for 7 h under an H2 atmosphere, filtered through Celite® and concentrated in vacuo. A mixture contained the title compound along with starting material in a 7:3 ratio. MS: (MH+)=227.1; Calc'd 227.69 for C11H15ClNO2.

Workup

  1. filtrationfiltered through Celite®
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c7225cdc2fe47c689dbb9e3bb017bbd
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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