Sodium Hydroxide → HCID 68773802, compound

HRID 1711182Notes

Reaction equation

HRID 1711182 reaction equation
[CH3:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([CH3:11])[C:3]=1[C:12]#N.N([O-])=[O:15].[Na+].[OH-:18].[Na+]>OS(O)(=O)=O.O>[CH3:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([CH3:11])[C:3]=1[C:12]([OH:15])=[O:18]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 68778454HCID 68778454, compound

Product 1

HCID 68773802HCID 68773802, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
120 °C

Procedure

The above-prepared nitrile (500 mg, 2.9 mmol) was dissolved in a mixture of H2SO4 (conc. 4 ml) and H2O (1 ml). The mixture was heated at 120° C. for 16 h. It was then cooled to 90° C. and NaNO2 (1.4 g, 20 mmol) was added in small portions over 10 min. The reaction was heated at 90° C. for and additional 1 h and then cooled to rt and poured into an ice-water mixture (˜20 ml). The chilled mixture was basified to PH=12 using 10N NaOH. The aqueous mixture was then washed with CH2Cl2 (15 ml×2) to remove impurities. It was then acidified to PH=2. After being concentrated under high vacuum to dryness, the residue was extracted with CH2Cl2/CH3OH (4/1, 30 ml×3). The combined extracts were concentrated to give 5,7-dimethyl-imidazo[1,2-a]pyridine-6-carboxylic acid (500 mg, 90% containing impurities) as a beige solid. 1H NMR (CDCl3) δ 2.56 (s, 3H), 2.83 (s, 3H), 7.74 (s, 1H), 8.08 (d, 1H, J=1.8 Hz), 8.22 (d, 1H, J=1.8 Hz).

Workup

  1. temperatureIt was then cooled to 90° C.
  2. temperatureThe reaction was heated at 90° C. for and additional 1 h
  3. temperaturecooled to rt
  4. washThe aqueous mixture was then washed with CH2Cl2 (15 ml×2)
  5. customto remove impurities
  6. concentrationAfter being concentrated under high vacuum to dryness
  7. extractionthe residue was extracted with CH2Cl2/CH3OH (4/1, 30 ml×3)
  8. concentrationThe combined extracts were concentrated

Sources & evidence

ORD record
ord-acc90fd471874d37bca3ff7e09110721
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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