Formic Acid → HCID 178497584, compound

HRID 1176559Notes

Reaction equation

HRID 1176559 reaction equation
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH:13](O)=O>Cl>[N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:3]([C:4]([O:6][CH3:7])=[O:5])[C:2]=2[NH:1][CH:13]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 5718252,3-Diaminobenzoic acid methyl ester

Product 1

HCID 178497584HCID 178497584, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2.000 g of methyl 2,3-diaminobenzoate are suspended in 35 ml of 4M aqueous HCl. The suspension is admixed at room temperature with 1.350 ml of formic acid and heated to reflux over one hour. The reaction solution is cooled to room temperature and the precipitated solid is filtered off. The filtercake is taken up in 50 ml of methanol and the mixture is heated to reflux until all solids have dissolved. The hot solution is treated with 0.500 g of activated carbon and subsequently clarified by filtration. The filtrate is admixed with 0.62 ml of conc. H2SO4 and heated to reflux over 24 hours. The reaction solution is cooled to room temperature and made neutral with saturated aqueous sodium carbonate solution (6 ml). The mixture is subsequently admixed with 50 ml of water and 100 ml of ethyl acetate, and the phases are separated. The aqueous phase is extracted with ethyl acetate (2×100 ml) and the combined organic phases are subsequently washed with 100 ml of saturated sodium carbonate solution and 100 ml of water, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a beige solid. Rt=2.02.

Workup

  1. temperatureheated
  2. temperatureto reflux over one hour
  3. filtrationthe precipitated solid is filtered off
  4. temperaturethe mixture is heated
  5. temperatureto reflux until all solids
  6. dissolutionhave dissolved
  7. additionThe hot solution is treated with 0.500 g of activated carbon
  8. filtrationsubsequently clarified by filtration
  9. temperatureheated
  10. temperatureto reflux over 24 hours
  11. temperatureThe reaction solution is cooled to room temperature
  12. customthe phases are separated
  13. extractionThe aqueous phase is extracted with ethyl acetate (2×100 ml)
  14. washthe combined organic phases are subsequently washed with 100 ml of saturated sodium carbonate solution and 100 ml of water
  15. dry with materialdried over sodium sulphate
  16. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-66d22d303ee24f61aca1d7bf943b7a36
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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