Formic Acid → HCID 83524259, compound

HRID 590389Notes

Reaction equation

HRID 590389 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]#N)=[CH:13][C:8]=2[N:7]=[N:6]1.C(O)=[O:17]>O>[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH:14]=[O:17])=[CH:13][C:8]=2[N:7]=[N:6]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 89553772HCID 89553772, compound2×

Product 1

HCID 83524259HCID 83524259, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 500 mg (2.47 mmol) of 1-(3-hydroxypropyl)-1H-1,2,3-benzotriazole-5-carbonitrile (Intermediate 18) and 550 mg of Ni—Al alloy 1:1 in 5.55 ml of 75% formic acid in water is stirred at 90° C. for 2.5 hr. After filtration and evaporation 10 ml of 2N NaOH and 10 ml of EtOH are added to the residue and the system is stirred at rt for 1.5 hr. The pH is made 6-7 by addition of 2N HCl and the system is extracted thoroughly with ethyl acetate. After washing with water, drying and concentrating, 0.35 g of 80% pure title compound (55% yield).

Workup

  1. filtrationAfter filtration and evaporation 10 ml of 2N NaOH and 10 ml of EtOH
  2. additionare added to the residue
  3. stirringthe system is stirred at rt for 1.5 hr
  4. additionby addition of 2N HCl
  5. extractionthe system is extracted thoroughly with ethyl acetate
  6. washAfter washing with water
  7. customdrying
  8. concentrationconcentrating

Sources & evidence

ORD record
ord-e93847c5356a4d1688cac0acc1375309
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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