Acetic Acid → HCID 22843823, compound

HRID 1195728Notes

Reaction equation

HRID 1195728 reaction equation
[OH:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[O:11][C:12]1[C:13]2[N:14]([C:18]([N:22]=O)=[C:19]([CH3:21])[N:20]=2)[CH:15]=[CH:16][CH:17]=1.C(O)(=O)C.C(=O)([O-])O.[Na+]>[Zn].O>[NH2:22][C:18]1[N:14]2[CH:15]=[CH:16][CH:17]=[C:12]([O:11][C@@H:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[CH2:10][C@H:2]3[OH:1])[C:13]2=[N:20][C:19]=1[CH3:21]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 22843826HCID 22843826, compound

Product 1

HCID 22843823HCID 22843823, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

0.5 g of 8-(2-(trans)-hydroxy-2,3-dihydro-1-indenyloxy)-2-methyl-3-nitroso-imidazo[1,2-a]pyridine is dissolved in a mixture consisting of 10 ml glacial acetic acid and 3 ml water and 0.5 g commercial zinc powder is added at 0° C. waterbath temperature. After one hour the solution is diluted with 100 ml icewater adjusted to pH 8 with saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The combined extracts are dried over potassium carbonate. After removal of the solvent in vacuo, the mixture is purified over silica gel (methylene chloride/methanol=98/02). After recrystallization from ethanol the title compound of 125°-127° C. is obtained.

Workup

  1. additionis added at 0° C. waterbath temperature
  2. additionAfter one hour the solution is diluted with 100 ml
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts are dried over potassium carbonate
  5. customAfter removal of the solvent in vacuo
  6. customthe mixture is purified over silica gel (methylene chloride/methanol=98/02)
  7. customAfter recrystallization from ethanol the title compound of 125°-127° C.
  8. customis obtained

Sources & evidence

ORD record
ord-46a6a29483ce4a539758bd0647f35a3a
Source dataset
uspto-grants-1992_05
Patent number
US05112834

Reaction notes

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