Formic Acid → HCID 178432647, compound

HRID 1047294Notes

Reaction equation

HRID 1047294 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9](=[NH:12])[NH:10][NH2:11])=[N:6][C:7]=1[CH3:8].[CH:13](O)=O>CO>[Br:1][C:2]1[C:7]([CH3:8])=[N:6][C:5]([C:9]2[NH:12][CH:13]=[N:11][N:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 178432964HCID 178432964, compound

Product 1

HCID 178432647HCID 178432647, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

5-Bromo-6-methylpicolin-imido-hydrazide (1 equiv) and formic acid (15 equiv) were combined and heated with stirring at 100° C. for 6 h. The reaction was cooled to room temperature and diluted with methanol. The resulting slurry was stirred for 30 min and then partially concentrated under reduced pressure to ˜20% of the total volume. The resulting mixture was again diluted with methanol and partially concentrated under reduced pressure to ˜20% of the total volume. The resulting solids were collected by filtration, washed three times with water and dried under reduced pressure to provide the desired product in 84% yield, as an off-white solid. MS (ESI) m/z 238.9 [M]+, 240.9 [M+2]+.

Workup

  1. temperatureheated
  2. temperatureThe reaction was cooled to room temperature
  3. stirringThe resulting slurry was stirred for 30 min
  4. concentrationpartially concentrated under reduced pressure to ˜20% of the total volume
  5. additionThe resulting mixture was again diluted with methanol
  6. concentrationpartially concentrated under reduced pressure to ˜20% of the total volume
  7. filtrationThe resulting solids were collected by filtration
  8. washwashed three times with water
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-cc9e6d97fb434aa5b040808254e08e42
Source dataset
uspto-grants-2013_10
Patent number
US08569494B2

Reaction notes

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