Formic Acid → HCID 178422430, compound

HRID 400720Notes

Reaction equation

HRID 400720 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[C:4]([CH3:10])[CH:3]=1.[CH:11](O)=O>>[Br:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]2[NH:9][CH:11]=[N:8][C:6]=2[CH:7]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 15163975-Bromo-3-methylbenzene-1,2-diamine

Product 1

HCID 178422430HCID 178422430, compoundYield 97%

Procedure

A solution of 5-bromo-3-methyl-benzene-1,2-diamine (Maybridge, 3 g; 14.92 mmol) in formic acid (75 mL) was heated at reflux for 16 hours. Reaction mixture was concentrated under vacuum to give a brown oil. It was extracted by EtOAc from a saturated aqueous solution of NaHCO3, dried over MgSO4 and evaporated under vacuum to give the title compound as a pale yellow solid (3.07 g, 97%). 1H NMR (DMSO-d6) δ 12.92-12.34 (bs, 1H), 8.22 (s, 1H), 7.59 (br s, 1H), 7.17 (s, 1H), 3.33 (s, 3H). LC/MS (Method B): 211.0 (M+H)+.

Workup

  1. temperatureat reflux for 16 hours
  2. customReaction mixture
  3. concentrationwas concentrated under vacuum
  4. customto give a brown oil
  5. extractionIt was extracted by EtOAc from a saturated aqueous solution of NaHCO3
  6. dry with materialdried over MgSO4
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-4ab02838b16445c9ac9e7641b24f9b5f
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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