Sodium Carbonate → 2-Chloro-3-methoxyaniline

HRID 646555Notes

Reaction equation

HRID 646555 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 2c2 (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 CH2Cl(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 2c3 (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 CH2Cl(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-bc93129e03c447949633c2b79324941f
Source dataset
uspto-grants-2010_04
Patent number
US07705146B2

Reaction notes

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