Sodium Bicarbonate → HCID 135555945, compound

HRID 1061726Notes

Reaction equation

HRID 1061726 reaction equation
N[C:2]1[CH:3]=[C:4]2[CH2:17][CH2:16][CH2:15][C:6]3=[N:7][N:8]([CH2:11][CH:12]([OH:14])[CH3:13])[C:9]([CH:10]=1)=[C:5]23.N([O-])=[O:19].[Na+].C([O-])(O)=O.[Na+]>OS(O)(=O)=O.O.O>[OH:14][CH:12]([CH3:13])[CH2:11][N:8]1[C:9]2[CH:10]=[C:2]([OH:19])[CH:3]=[C:4]3[C:5]=2[C:6]([CH2:15][CH2:16][CH2:17]3)=[N:7]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 22285727HCID 22285727, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 135555945HCID 135555945, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 21910475Sulfuric acid hydrate (1:1)Solvent

Conditions

Temperature
0 °C

Procedure

The product from Step D (1.90 g, 8.4 mmol) was dissolved in H2SO4/H2O (1:2, 60 mL) and cooled to 0° C. A solution of NaNO2 (0.64 g, 9.2 mmol) in H2O (2.0 mL) was added dropwise and the resultant dark solution was stirred for 2 h. Water (40 mL) was added to this solution and the mixture was heated to 110° C. for 2 h. After cooling the mixture to room temperature it was carefully neutralized with a saturated aqueous NaHCO3 solution and extracted with ethyl acetate (3×65 mL). The combined extracts were washed with brine (10 mL), dried (MgSO4) and evaporated to a residue which was purified by column chromatography (silica, 50% to 60% gradient of ethyl acetate in hexane) to give a solid (1.2 g, 83%): m.p: 153-155° C.; MS (ES) m/z 233(M+); 1H NMR (CDCl3) δ 9.39 (1H, s), 6.50 (1H, s), 6.34 (1H, s), 4.84 (1H, d, J=4.0 Hz), 4.00 (3H, m), 2.76 (2H, q, j=6.0 Hz), 2.01 (2H, m), 1.01 (3H, d, J=6.0 Hz).

Workup

  1. temperaturethe mixture was heated to 110° C. for 2 h
  2. temperatureAfter cooling the mixture to room temperature it
  3. extractionextracted with ethyl acetate (3×65 mL)
  4. washThe combined extracts were washed with brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated to a residue which
  7. customwas purified by column chromatography (silica, 50% to 60% gradient of ethyl acetate in hexane)

Sources & evidence

ORD record
ord-bf7adc2451364567ada8fd2ca37ebfdd
Source dataset
uspto-grants-2005_11
Patent number
US06960608B2

Reaction notes

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