Hydrochloric Acid → HCID 90426657, compound

HRID 718130Notes

Reaction equation

HRID 718130 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([O:9][C:10]2[C:11]([CH3:31])=[N:12][C:13]([NH:16][N:17]=C(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:14][CH:15]=2)[CH:6]=[CH:5][N:4]=1>C1(C)C=CC=CC=1>[Cl:2][C:3]1[CH:8]=[C:7]([O:9][C:10]2[C:11]([CH3:31])=[N:12][C:13]([NH:16][NH2:17])=[CH:14][CH:15]=2)[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90427662HCID 90427662, compound

Product 1

HCID 90426657HCID 90426657, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Concentrated HCl (21.31 mL, 256 mmol) was added to a solution of Example A2 (4.2 g, 10.1 mmol) in toluene (80 mL) and the reaction mixture was stirred at 110° C. for 1.5 h. The organic solvent was removed in vacuo and the remaining aqueous solution was diluted with water (50 mL), washed with toluene (2×20 mL), cooled in an ice bath, and adjusted to pH ˜12 with 50% NaOH (aq). The suspension was saturated with solid NaCl and extracted with EtOAc (3×50 mL). The combined organics were dried (Na2SO4) and concentrated in vacuo to afford 3-((2-chloropyridin-4-yl)oxy)-6-hydrazinyl-2-methylpyridine (2.1 g, 83%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.24 (d, J=5.7 Hz, 1H), 7.50 (s, 1H), 7.30 (d, J=8.8 Hz, 1H), 6.88 (d, J=2.2 Hz, 1H), 6.85-6.84 (m, 1H), 6.63 (d, J=9.0 Hz, 1H), 4.13 (br s, 2H), 2.09 (s, 3H); MS (ESI) m/z: 251.1 (M+H+).

Workup

  1. customThe organic solvent was removed in vacuo
  2. additionthe remaining aqueous solution was diluted with water (50 mL)
  3. washwashed with toluene (2×20 mL)
  4. temperaturecooled in an ice bath
  5. extractionextracted with EtOAc (3×50 mL)
  6. dry with materialThe combined organics were dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-764fe82b7545455ba2b2eaafde3013cd
Source dataset
uspto-grants-2015_11
Patent number
US09193719B2

Reaction notes

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