Ethyl Acetate → 2-fluoro-N1-(3-morpholinopropyl)benzene-1,4-diamine

HRID 56165Notes

Reaction equation

HRID 56165 reaction equation
[F:1][C:2]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:3]=1[NH:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.CCOC(C)=O>[Pd].CO>[F:1][C:2]1[CH:17]=[C:16]([NH2:18])[CH:15]=[CH:14][C:3]=1[NH:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 29277432-fluoro-N-(3-morpholinopropyl)-4-nitroaniline

Product 1

HCID 431684652-fluoro-N1-(3-morpholinopropyl)benzene-1,4-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-fluoro-N-(3-morpholinopropyl)-4-nitroaniline (1.78 g, 6.28 mmol) in mixed solvents of EtOAc (15 mL) and MeOH (15 mL) was added catalyst Pd/C (0.30 g). The reaction was stirred at rt under H2 for 2 h, 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-60f431a2f98345b1b92c44836d7122b0
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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