Formic Acid → HCID 67151216, compound

HRID 2404249Notes

Reaction equation

HRID 2404249 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:12])[C:10]=1[NH2:11])[C:5]([O-:7])=[O:6].[CH:13](O)=O.[OH-].[K+]>O>[Cl:12][C:9]1[C:10]2[N:11]=[CH:13][NH:1][C:2]=2[CH:3]=[C:4]([C:5]([OH:7])=[O:6])[CH:8]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 14797Potassium HydroxideHCID 86653286HCID 86653286, compound

Product 1

HCID 67151216HCID 67151216, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,4-diamino-5-chlorobenzoate (1.2 g. 6 mmol) was added to water (10 mL) and formic acid (826 mg, 18 mmol) and heated at reflux for 4 hours. The reaction was cooled to ambient temperature and aqueous potassium hydroxide was added (21 mL, 1M). The reaction solution was washed with ethyl acetate (2×25 mL each). The aqueous layer was acidified to pH=5 with aqueous hydrochloric acid (1N) to give a precipitate which was filtered, washed with water and dried under a stream of nitrogen to give the title compound (439 mg, 37%). 1H NMR (400 MHz, DMSO-d) δ ppm 8.45 (s, 1H) 8.10 (d, J=1.17 Hz, 1H) 7.77 (d, J=1.37 Hz, 1H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. washThe reaction solution was washed with ethyl acetate (2×25 mL each)
  4. customto give a precipitate which
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried under a stream of nitrogen

Sources & evidence

ORD record
ord-2d53c2e6ee0b44449bbeac2e34719a4d
Source dataset
uspto-grants-2014_08
Patent number
US08802690B2

Reaction notes

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