Methane → 6-Amino-2,3-dimethoxybenzoic acid

HRID 542611Notes

Reaction equation

HRID 542611 reaction equation
[C:1]([C:5]1[C:17]([O:18][CH3:19])=[C:16]([O:20][CH3:21])[CH:15]=[CH:14][C:6]=1[N:7](C(=O)C)C(=O)C)([O:3]C)=[O:2].[OH-].[Na+].C>C(O)(=O)C>[CH3:21][O:20][C:16]1[C:17]([O:18][CH3:19])=[C:5]([C:1]([OH:3])=[O:2])[C:6]([NH2:7])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 14798Sodium HydroxideHCID 138534852-carbomethoxy-N,N-diacetyl-3,4-dimethoxyaniline

Product 1

HCID 117455906-Amino-2,3-dimethoxybenzoic acidYield 60.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 36.8 g (130 mmol) of 2-carbomethoxy-N,N-diacetyl-3,4-dimethoxyaniline and 500 mL of 2N NaOH was prepared and heated to reflux to obtain a clear brown solution. After refluxing for 5 hours, the reaction mixture was treated with Darco and filtered through a Hyflo bed to give a clear yellow solution. Glacial acetic acid (65 mL) was added and the reaction mixture was extracted with 2×500 mL of methylene chloride. Drying over sodium sulfate and rotary evaporation gave 19.5 g (76%) of crude white product. Recrystallization from ethyl acetate-hexane gave 15.4 g (60%) of the product as a white crystalline solid, mp 92.5°-95.0° C. NMR (CDCl3) δ 3.78 (s, 3H, OCH3), 4.02 (s, 3H, OCH3), 6.45 (d, 1H, J=10 Hz, ArH), 7.00 (d, 1H, J=10 Hz, ArH), 7.60 (br s, 3 H, CO2H and NH2).

Workup

  1. customwas prepared
  2. temperatureheated
  3. temperatureto reflux
  4. customto obtain a clear brown solution
  5. temperatureAfter refluxing for 5 hours
  6. filtrationfiltered through a Hyflo bed
  7. customto give a clear yellow solution
  8. extractionthe reaction mixture was extracted with 2×500 mL of methylene chloride
  9. dry with materialDrying over sodium sulfate and rotary evaporation
  10. customgave 19.5 g (76%) of crude white product
  11. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b179f078644d4371b1f8e2550da7c6a6
Source dataset
uspto-grants-1987_04
Patent number
US04658054

Reaction notes

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