Hydrochloric Acid → HCID 15463562, compound

HRID 1005458Notes

Reaction equation

HRID 1005458 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[NH:13][C:12](=[O:14])[C:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[OH-:27].[Na+].OO.Cl>CCO>[NH2:2][C:1]([C:3]1[CH:4]=[C:5]([C:9]2[NH:13][C:12](=[O:14])[C:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:10]=2)[CH:6]=[CH:7][CH:8]=1)=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 15463557HCID 15463557, compound

Product 1

HCID 15463562HCID 15463562, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 50 mL flask was added 0.300 g (0.889 mmol) of the 3-cyano derivative (Example 2) and 6 mL of 95% EtOH. The solution was stirred until homogeneous and then 1 mL of 6M NaOH and 1 mL of 30% hydrogen peroxide were added and the rxn was heated to reflux and allowed to stir for 3 h. Upon completion the reaction was cooled to rt and neutralized with conc. HCl. The solvent was evaporated in vacuo, and the crude residue was purified by column chromatography (Silica gel/Hexanes:Acetone 4:1) producing 0.20 g (63%) of the desired amide as a white solid. LRMS m/z (ESI) 356.2 (M+H)+ ; 1H-NMR (DMSO-d6, 300MHz) δ=8.74 (s, 1H), 8.32 (d, 1H, J=6.0 Hz), 8.10 (d, 1H, J=6.0 Hz), 7.66 (t, 1H, J=6.0 Hz), 7.48 (d, 4H, J=6.0 Hz), 7.33 (m, 6H).

Workup

  1. additionwere added
  2. temperaturethe rxn was heated
  3. temperatureto reflux
  4. customThe solvent was evaporated in vacuo
  5. customthe crude residue was purified by column chromatography (Silica gel/Hexanes:Acetone 4:1)

Sources & evidence

ORD record
ord-5665e861efe54d439b936ff5c2e118a6
Source dataset
uspto-grants-2000_04
Patent number
US06054590

Reaction notes

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