Sodium Hydroxide → HCID 15573080, compound

HRID 1733226Notes

Reaction equation

HRID 1733226 reaction equation
[C:1]([C:5]1[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8]([OH:18])=[CH:7][N:6]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)([O:3]C)=[O:2].[OH-].[Na+]>CO>[C:1]([C:5]1[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8]([OH:18])=[CH:7][N:6]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15573072HCID 15573072, compound

Product 1

HCID 15573080HCID 15573080, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 30 ml of methanol was dissolved 1.0 g of the product of Example 2 followed by addition of 2 ml of 10% aqueous sodium hydroxide. The mixture was refluxed at water bath temperature for 6 hours and the methanol then removed by distillation. The residue was neutralized with a 10% aqueous hydrochloric acid and the resultant crystals were recovered by filtration and recrystallized from methanoltetrahydrofuran to yield 630 mg of the title compound as colorless needles, m.p. 158°-159° C. (decomp.). Mol. wt. (based on mass spectrum) 228. Elemental analysis found: C, 63.32%; H, 3.28%; N, 12.05%; calculated for C12H8N2O3 : C, 63.16%; H, 3.53%; N, 12.28%. The IR absorption spectrum shows the absorption at 1680 cm-1 in starting compound has disappeared with absorption observed at 1610 cm-1 (carbonyl).

Workup

  1. temperatureThe mixture was refluxed at water bath temperature for 6 hours
  2. customthe methanol then removed by distillation
  3. filtrationthe resultant crystals were recovered by filtration
  4. customrecrystallized from methanoltetrahydrofuran

Sources & evidence

ORD record
ord-f2e805540d9e4739b0236868d48845f0
Source dataset
uspto-grants-1980_12
Patent number
US04241064

Reaction notes

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