Formic Acid → HCID 59208360, compound

HRID 2243074Notes

Reaction equation

HRID 2243074 reaction equation
[CH:1]([OH:3])=[O:2].OO.[Cl:6][C:7]1[CH:17]=[C:16](C=O)[C:10]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[CH:9][N:8]=1>>[Cl:6][C:7]1[CH:17]=[C:16]([C:10]([C:11](=[O:12])[N:13]([CH3:14])[CH3:15])=[CH:9][N:8]=1)[C:1]([OH:3])=[O:2]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 784Hydrogen PeroxideHCID 59208508HCID 59208508, compound2×

Product 1

HCID 59208360HCID 59208360, compoundYield 37.1%

Procedure

Formic acid (0.628 mL, 16.5 mmoles) and 30% hydrogen per oxide (1.87 mL, 16.5 mmoles) were added to 6-chloro-4-formyl-N,N-dimethyl-nicotinamide (Intermediate 67, 0.7 g. 3.3 mmoles), and the solution was kept at 4° C. for 4 days. The precipitate was filtered and washed with cold water. The solid was heated to reflux in toluene then collected by filtration (2×25 mL) to afford 0.28 g (35.89%) of the title compound as pale yellow solid. MS (APCI): 229 (M+H+) for C9H9ClN2O3; NMR: 2.76 (s, 3H), δ 2.97 (s, 3H), δ 7.84 (s, 1H), δ 8.47 (s, 1H).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with cold water
  3. temperatureThe solid was heated
  4. temperatureto reflux in toluene
  5. filtrationthen collected by filtration (2×25 mL)

Sources & evidence

ORD record
ord-966038c01a75402ca72bb68d9e10953e
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

Loading…