Hydrochloric Acid → HCID 49783990, compound

HRID 1097218Notes

Reaction equation

HRID 1097218 reaction equation
[CH3:1][N:2]([N:4]=[N:5][C:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[Se:8][C:7]=1[C:15]([O:17]CC)=[O:16])[CH3:3].[OH-].[Na+].Cl>CO.O>[CH3:3][N:2]([N:4]=[N:5][C:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[Se:8][C:7]=1[C:15]([OH:17])=[O:16])[CH3:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59547217HCID 59547217, compound

Product 1

HCID 49783990HCID 49783990, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 3-[(dimethylamino)diazenyl]selenopheno[2,3-b]pyridine-2-carboxylate (170 mg, 0.52 mmol), prepared as described in Example 6 step b) in methanol (10 mL) was added a solution of sodium hydroxide (83 mg, 2.08 mmol) in water (2 mL) and stirred at room temperature (rt) for 2 h. The mixture was diluted with ice cold water and acidified with dil. HCl. The mixture was stirred for 30 min and extracted with ethyl acetate (3×100 mL). The combined organic layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using chloroform-methanol (95:5) as eluents to give the product, which was recrystallized from chloroform-methanol-hexane as a light brown color solid (30 mg, 20%), mp 172-174° C. IR (KBr) νmax 3427, 3025, 2919, 1707, 1265, 1218, 1013, 863 cm−1; 1H NMR (400 MHz, DMSO-d6): δ 13.09 (1H, br s, —COOH), 8.65-8.69 (2H, m, H-4,6), 7.53 (1H, dd, J=8.2, 4.6 Hz, H-5), 3.67 (3H, s, —NCH3), 3.29 (3H, s, —NCH3); LC-MS (positive ion mode): m/z 319, 321 (M+Na)+.

Workup

  1. additionThe mixture was diluted with ice cold water
  2. stirringThe mixture was stirred for 30 min
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washThe combined organic layer was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationThe solution was filtered
  7. customevaporated the solvent
  8. customThe residue was chromatographed over silica gel column
  9. customto give the product, which
  10. customwas recrystallized from chloroform-methanol-hexane as a light brown color solid (30 mg, 20%), mp 172-174° C

Sources & evidence

ORD record
ord-03a1ed6f3a6443ed91879d6e1f7a3cbd
Source dataset
uspto-grants-2012_03
Patent number
US08143237B2

Reaction notes

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