Formic Acid → HCID 178505413, compound

HRID 400717Notes

Reaction equation

HRID 400717 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH2:9])=[C:6]([F:8])[CH:7]=1.[CH:11](O)=O>>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]2[NH:9][CH:11]=[N:10][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 27732795-Bromo-3-fluorobenzene-1,2-diamine

Product 1

HCID 178505413HCID 178505413, compoundYield 92%

Procedure

A solution of 5-bromo-2,3-diaminofluorobenzene (Apollo, 3 g; 14.63 mmol) in formic acid (75 mL) was heated at reflux overnight after which the reaction mixture was concentrated under vacuum to give a brown oil. It was extracted with EtOAc from a saturated aqueous solution of NaHCO3, dried over MgSO4 and evaporated under vacuum to give the title compound as a light pink solid (2.91 g, 92%). 1H NMR (DMSO-d6): δ 8.30 (s, 1H), 7.62 (d, J=1.5 Hz, 1H), 7.27 (dd, J=10.3, 1.5 Hz, 2H), 3.32 (bs, 2H). HPLC (Method A), Rt: 2.09 min (purity: 97.4%). LC/MS (Method B): 216.9 (M+H)+.

Workup

  1. temperatureat reflux overnight after which the reaction mixture
  2. concentrationwas concentrated under vacuum
  3. customto give a brown oil
  4. extractionIt was extracted with EtOAc from a saturated aqueous solution of NaHCO3
  5. dry with materialdried over MgSO4
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-b93d520f8c954c39836d03b09e91d235
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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