Hydrochloric Acid → HCID 123148243, compound

HRID 1916853Notes

Reaction equation

HRID 1916853 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:15])=[C:9]([C:11]([NH:13][NH2:14])=[O:12])[N:10]=2)[CH:7]=1.Cl.[N:17]([O-])=O.[Na+].C([O-])(O)=O.[Na+]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:15])=[C:9]([C:11]([N:13]=[N+:14]=[N-:17])=[O:12])[N:10]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 67953970HCID 67953970, compound

Product 1

HCID 123148243HCID 123148243, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 6-A (1.8 g, 8.65 mmol) was dissolved in 2N HCl (21.6 mL, 43.2 mmol) and cooled in an ice bath. A solution of NaNO2 (0.716 g, 10.4 mmol) in water (3 mL) was added dropwise over 5 minutes and the resultant solution was stirred on the ice bath for 25 minutes, then made basic with careful addition of a saturated aqueous solution of NaHCO3. A solid precipitate was collected by filtration, then dissolved in CH2Cl2 and dried over Na2SO4. The solvent was evaporated in vacuo to afford compound 6-B as a cream colored solid (1.86 g, 98%). 1H-NMR (CDCl3): δ 7.81-7.87 (m, 1H), 7.64 (dd, J=10.0, 5.2 Hz, 1H), 7.16-7.25 (m, 1H), 2.80 (s, 3H); MS: m/z 220.1 (MH+).

Workup

  1. temperaturecooled in an ice bath
  2. filtrationA solid precipitate was collected by filtration
  3. dissolutiondissolved in CH2Cl2
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-e179b7db8e084f32900e7a5c4e519aa8
Source dataset
uspto-grants-2013_12
Patent number
US08618150B2

Reaction notes

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