Sodium Carbonate → 2-Chloro-3-methoxyaniline

HRID 642740Notes

Reaction equation

HRID 642740 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH3:12].C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C.C(O)C.O.[Fe]>[Cl:1][C:2]1[C:3]([O:11][CH3:12])=[CH:4][CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

7

Reactant 2

HCID 10340Sodium CarbonateHCID 124118272-Chloro-1-methoxy-3-nitrobenzene

Product 1

HCID 225046772-Chloro-3-methoxyanilineYield 103.5%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-Chloro-3-nitroanisole 1c2 (1.38 g; 7.36 mmol) was dissolved in a mixture of glacial acetic acid (19 mL)/ethanol (19 mL). To this solution was added iron powder (1.64 g; 29.4 mmol). The mixture was stirred at reflux for 3.5 hr and worked up. The reaction mixture was diluted with water (70 mL), neutralized with solid Na2CO3 and the product extracted with CH2Cl2 (3×150 mL). The extracts were combined and washed with sat. brine and then dried over (Na2SO4), filtered and concentrated in vacuo to afford the crude product, 2-chloro-3-methoxyaniline 1c3 (100%; 1.2 g) as a yellow oil. This material was used as such in the following steps. MS 157.9 (MH)+; Homogeneity by HPLC (TFA)@220 nm: 86%.

Workup

  1. temperatureat reflux for 3.5 hr
  2. extractionthe product extracted with CH2Cl2 (3×150 mL)
  3. washwashed with sat. brine
  4. dry with materialdried over (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5cc72dd7cff944db9115f81ecf3020f7
Source dataset
uspto-grants-2010_04
Patent number
US07696242B2

Reaction notes

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