1-(3-Chloro-propoxy)-2-nitro-benzene → 2-(3-chloropropoxy)aniline

HRID 1984215Notes

Reaction equation

HRID 1984215 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O.[H][H]>C(O)C.[Pt](=O)=O>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH2:12]

Participants

5

Reactant 2

HCID 114244631-(3-Chloro-propoxy)-2-nitro-benzeneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 100126432-(3-chloropropoxy)aniline

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

1-(3-Chloro-propoxy)-2-nitro-benzene (˜60 mmol) is dissolved in ethanol (200 ml) and platinum dioxide (0.5 g) is added. The stirred mixture is treated with hydrogen under normal pressure until the hydrogen uptake stopped. The catalyst is filtered off and the filtrate is evaporated. A pale yellow oil with Rf=0.3 (CH2Cl2) is obtained, which is used in the next step without further purification.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customA pale yellow oil with Rf=0.3 (CH2Cl2) is obtained
  4. customwhich is used in the next step without further purification

Sources & evidence

ORD record
ord-03d270c511684d089af6b1252f028270
Source dataset
uspto-grants-2009_06
Patent number
US07544688B2

Reaction notes

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