Methanol → Methyl 2-amino-3-nitrobenzoate

HRID 1757124Notes

Reaction equation

HRID 1757124 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:18]O>>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:18])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2196332-Amino-3-nitrobenzoic acid

Product 1

HCID 607264Methyl 2-amino-3-nitrobenzoate

Procedure

18 g (99 mmol) of the compound from Example 1 b) are stirred under reflux in 200 ml of methanol with 20 ml of thionyl chloride for 48 h. The reaction solution is evaporated in a rotary evaporator, the residue is taken up in 400 ml of satd. Na2CO3 solution, the solution is extracted 3 times with EA, and the combined organic phases are washed with dilute Na2CO3 solution and satd. NaCl solution, dried over Na2SO4 and concentrated. Chromatography on SiO2 with EA/Hep 9:1 and 7:3 yields 11.5 g of the title compound.

Workup

  1. customThe reaction solution is evaporated in a rotary evaporator
  2. extractionNa2CO3 solution, the solution is extracted 3 times with EA
  3. washthe combined organic phases are washed with dilute Na2CO3 solution
  4. dry with materialNaCl solution, dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fdb3356f0b2b491989ef77c690a2fc80
Source dataset
uspto-grants-1995_08
Patent number
US05444068

Reaction notes

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