3-chloro-N-(2-morpholinoethyl)-4-nitroaniline → 3-chloro-N1-(2-morpholinoethyl)benzene-1,4-diamine

HRID 56162Notes

Reaction equation

HRID 56162 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[NH:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[CH:14]=[CH:15][C:16]=1[NH2:17]

Participants

4

Reactant 1

HCID 900233253-chloro-N-(2-morpholinoethyl)-4-nitroaniline

Product 1

HCID 900225353-chloro-N1-(2-morpholinoethyl)benzene-1,4-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-chloro-N-(2-morpholinoethyl)-4-nitroaniline (3.50 g, 12.25 mmol) in EtOAc (60 mL) was added catalyst Pd/C (0.73 g). The reaction was stirred at rt under H2 overnight, then filtered. The filtrate was concentrated in vacuo to give the crude product for the next step without further purification.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-93ebbf072ed644d4967deae5a740e95e
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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