Sodium Carbonate → 2-Chloro-3-methoxyaniline

HRID 1988563Notes

Reaction equation

HRID 1988563 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 C3 (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 saturated. brine and then dried over (Na2SO4), filtered and concentrated in vacuo to afford the crude product, 2-chloro-3-methoxyaniline C4 (100%; 1.2 g) as a yellow oil. This material was used as such in the following steps.

Workup

  1. temperatureat reflux for 3.5 hr
  2. extractionthe product extracted with CH2Cl2 (3×150 mL)
  3. washwashed with saturated
  4. dry with materialbrine and then dried over (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b3e94abf4f3647ba9c1f3ae168f34f95
Source dataset
uspto-grants-2010_01
Patent number
US07642235B2

Reaction notes

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