HCID 470751, compound → HCID 178462465, compound

HRID 724958Notes

Reaction equation

HRID 724958 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:29])[C:7](=[O:28])[C:8]3[CH:18]=[C:17]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][N:24]=[C:23](N)[CH:22]=4)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.N([O-])=[O:31].[Na+]>S(=O)(=O)(O)O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:29])[C:7](=[O:28])[C:8]3[CH:18]=[C:17]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][N:24]=[C:23]([OH:31])[CH:22]=4)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1

Participants

5

Reactant 2

HCID 470751HCID 470751, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178462465HCID 178462465, compoundYield 36.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

The product of Example 71 (14 mg, 0.03 mmol) was dissolved in conc. sulfuric acid (0.06 mL) and water (0.5 mL), and the resultant solution was cooled to 0° C. Sodium nitrite (2.9 mg, 0.04 mmol) was added, and the reaction mixture was warmed to room temperature. After 40 min, the product was extracted with ethyl acetate and recrystallized (ethyl acetate-hexanes) afforded the title compound (4.5 mg, 32%) as beige crystals, m.p. 243°-244° C.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. customrecrystallized (ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-b3124adf79b14f6d986dc27dbac9e362
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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