Hydrochloric Acid → HCID 57919203, compound

HRID 2381348Notes

Reaction equation

HRID 2381348 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[N:6](C2CCCCO2)[N:5]=[CH:4][C:3]=1[O:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19].Cl>CO.O>[Cl:1][C:2]1[C:7](=[O:8])[NH:6][N:5]=[CH:4][C:3]=1[O:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57919278HCID 57919278, compound

Product 1

HCID 57919203HCID 57919203, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2-[5-chloro-6-oxo-1-(tetrahydro-pyran-2-yl)-1,6-dihydro-pyridazin-4-yloxy]-benzonitrile (61.8 g, 0.19 mol) in methanol (370 mL) was treated with a 6N aqueous hydrochloric acid solution (185 mL). The reaction was stirred at 90° C. for 4 h and then was allowed to cool to 25° C. The reaction was diluted with water. The resulting precipitate was collected by filtration, washed with water and dried in vacuo to afford 2-(5-chloro-6-oxo-1,6-dihydro-pyridazin-4-yloxy)-benzonitrile (43.1 g, 94%); ESI-MS 248 [M+H+]; HPLC: >99% (purity). 1H-NMR (300 MHz, DMSO-d6) δ 13.63 (s, 1H), 7.96-7.99 (m, 2H), 7.71-7.77 (m, 1H), 7.37-7.45 (m, 2H).

Workup

  1. temperatureto cool to 25° C
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d22259916b6f4698b9f1bba305add583
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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