Hydrochloric Acid → HCID 83524259, compound

HRID 590409Notes

Reaction equation

HRID 590409 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.CO.C(=O)([O-])[O-:19].[K+].[K+].Cl>C(O)=O.O.[Ni].[Al]>[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH:14]=[O:19])=[CH:13][C:8]=2[N:7]=[N:6]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 11430Potassium CarbonateHCID 89553772HCID 89553772, compound2×

Product 1

HCID 83524259HCID 83524259, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 6336846Nickel aluminideCatalystHCID 284Formic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 1-(3-hydroxypropyl)-1H-1,2,3-benzotriazole-5-carbonitrile (Intermediate 97, 9.6 g, 47.5 mmol) in aqueous Formic Acid (106 mL of a 75% solution in water) was added Niquel-Aluminium alloy (10.6 g, 0.12 mol). The mixture was stirred overnight at 75° C. The solids were removed by filtration through Celite® and the solvent was removed under reduced pressure. The crude obtained was treated with MeOH (415 mL) and potassium carbonate was added (49 g, 0.35 mol). After 1 h the solution was acidified with 2N HCl until neutral pH and MeOH evaporated under reduced pressure. The aqueous phase was extracted with CH2Cl2 (3×200 mL) and the resulting organic layer washed with water (2×50 mL), dried and evaporated under reduced pressure to afford the title compound as a solid (6.05 g, 60% yield), which was used in the next step without further purification.

Workup

  1. customThe solids were removed by filtration through Celite®
  2. customthe solvent was removed under reduced pressure
  3. customThe crude obtained
  4. additionwas added (49 g, 0.35 mol)
  5. customevaporated under reduced pressure
  6. extractionThe aqueous phase was extracted with CH2Cl2 (3×200 mL)
  7. washthe resulting organic layer washed with water (2×50 mL)
  8. customdried
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3439a6ba0e3848218edae67d7706ddb4
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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