Sulfuric Acid → HCID 178517129, compound

HRID 266931Notes

Reaction equation

HRID 266931 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([OH:11])[C:2]=1[OH:12].[N:13]([O-])=[O:14].[Na+].[OH-].[Na+].OS(O)(=O)=O>>[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[N:13][OH:14])[C:3](=[O:11])[C:2]1=[O:12]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 178515333HCID 178515333, compound

Product 1

HCID 178517129HCID 178517129, compoundYield 62.6%

Procedure

To a solution of 50.1 mg (0.311 mmol) of 11a and 52.0 mg (0.753 mmol) of NaNO2 in 1.5 mL of aqueous 0.2N NaOH in an ice-bath was added dropwise 1 mL of aqueous 2N H2SO4. A red precipitate was observed. The mixture was stirred in the ice-bath for 2 h and at 25° C. for 4 h, filtered and washed with water, and dried to leave 37 mg (62%) of 14a as a red solid, mp 241°-242° C. 1H NMR (CDCl3 +DMSO-d6), 6.83 (m, 2), 7.069 (t, 1, J=7.2), 8.544 (d, 1, J=8.1), 11.228 (m, 1). MS, 190 (100, M+), 162 (50), 145 (65), 117 (30). High resolution MS, Calcd for C9H6N2O3 190.0375, found 190.0377.

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-0884c230d0bc49c8b65d1c7863d9d618
Source dataset
uspto-grants-1997_07
Patent number
US05652368

Reaction notes

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