Hydrochloric Acid → HCID 67021570, compound

HRID 1661026Notes

Reaction equation

HRID 1661026 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:11][O:12][C:13](=[O:23])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=1[CH3:22].Cl.O1CCOCC1>CO.O1CCOCC1>[CH3:11][O:12][C:13](=[O:23])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:17][C:16]=1[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 796132-Chloro-3-nitropyridineHCID 21876486HCID 21876486, compound

Product 1

HCID 67021570HCID 67021570, compound

Reagents, catalysts & solvents 1

HCID 21966525Dioxane MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-3-nitro-pyridine (1.5 g, 9.46 mmol), (4-amino-2-methyl-phenyl)-acetic acid methyl ester (3.39 g 18.9 mmol, 2 equiv), and a 4 N solution of HCl in dioxane (6.9 mL, 28.0 mmol, 2.9 equiv) in MeOH/dioxane (30 mL; 1:1, v/v) is stirred for 54 h at 100° C. The reaction mixture is allowed to cool to rt and concentrated in vacuo. The residue is dissolved in EtOAc, washed with a saturated aqueous solution of NaHCO3, dried (Na2SO4), filtered and concentrated. Purification of the crude product by silica gel column chromatography (CH2Cl2/MeOH, 1:0→98:2) provides the title compound: ES-MS: 302.1 [M+H]+; tR=4.79 min (System 1); Rf=0.43 (CH2Cl2).

Workup

  1. temperatureto cool to rt
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue is dissolved in EtOAc
  4. washwashed with a saturated aqueous solution of NaHCO3
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the crude product by silica gel column chromatography (CH2Cl2/MeOH, 1:0→98:2)

Sources & evidence

ORD record
ord-8c3fb11bf57145cf9d8e584447a1e5e8
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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