Hydrochloric Acid → HCID 178525841, compound

HRID 1902499Notes

Reaction equation

HRID 1902499 reaction equation
[C:1]([O:10][CH2:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].Cl.[N:24]([O-])=O.[Na+].[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([OH:34])[C:29]=1[OH:35].C([O-])(=O)C.[Na+]>O1CCCC1.O.CO>[OH:34][C:30]1[CH:31]=[CH:32][C:33]([N:24]=[N:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([O:10][CH2:11][N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])=[O:9])=[N:28][C:29]=1[OH:35]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 20515576HCID 20515576, compoundHCID 23668193Sodium NitriteHCID 178516237HCID 178516237, compound

Product 1

HCID 178525841HCID 178525841, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Phthalimidomethyl anthranilate (1.0 g) was dissolved in 20 ml tetrahydrofuran (THF), concentrated hydrochloric acid added (1 ml) and the solution cooled in an ice bath. With rapid stirring sodium nitrite (0.23 g dissolved in 1 ml water) was added and the mixture stirred for another 20 minutes. This solution was then added dropwise to an ice-cooled solution of 2,3-pyridinediol (0.4 g) and sodium acetate (2.0 g) in 50 ml of a 2:1 mixture by volume of methanol and water. On further stirring for 1 hour at 0° C. the dye precipitated. It was further diluted with 100 ml water and the mixture filtered. The precipitate was washed with water and dried. Yield 1.2 g, m.p. 196°-201° C. A thin layer chromatogram showed a single spot.

Workup

  1. temperaturethe solution cooled in an ice bath
  2. additionwas added
  3. stirringOn further stirring for 1 hour at 0° C. the dye
  4. customprecipitated
  5. additionIt was further diluted with 100 ml water
  6. filtrationthe mixture filtered
  7. washThe precipitate was washed with water
  8. customdried

Sources & evidence

ORD record
ord-47783502b11b4f2795573315f18fd723
Source dataset
uspto-grants-1982_12
Patent number
US04363865

Reaction notes

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