Water → HCID 67171445, compound

HRID 872594Notes

Reaction equation

HRID 872594 reaction equation
[N+:1]([C:4]1[C:5]([C:21]#[N:22])=[N:6][CH:7]=[C:8]([C:10]2[N:14](C3CCCCO3)[N:13]=[CH:12][CH:11]=2)[CH:9]=1)([O-:3])=[O:2].O.C(=O)(O)[O-].[Na+]>Cl.CCO>[N+:1]([C:4]1[C:5]([C:21]#[N:22])=[N:6][CH:7]=[C:8]([C:10]2[NH:14][N:13]=[CH:12][CH:11]=2)[CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 70656353HCID 70656353, compound

Product 1

HCID 67171445HCID 67171445, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

3-Nitro-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)picolinonitrile (8.77 mmol) was dissolved in 10% HCl (g) in EtOH (15 ml) and stirred at RT overnight. 20 ml of water was added to the reaction mixture, followed by addition of sat. sodium bicarbonate solution until pH was neutral. Thus resulting precipitate was filtered, washed with water and dried in vacuum to yield 1.76 g (93%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 7.22 (m, 1H), 7.98 (m, 1H), 8.99 (d, 1H), 9.50 (d, 1H), 13.5 (bs, 1H).

Workup

  1. customThus resulting precipitate
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried in vacuum

Sources & evidence

ORD record
ord-db5a99ec93db4eb0ab2c5e47d648a321
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

Loading…