Hydrochloric Acid → HCID 4885471, compound

HRID 1660941Notes

Reaction equation

HRID 1660941 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:14][CH:13]=1.Cl.O1CCOC[CH2:24]1>CO.O1CCOCC1>[CH3:24][O:20][C:19](=[O:21])[CH2:18][C:15]1[CH:14]=[CH:13][C:12]([NH:11][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 145334-Aminophenylacetic acid2×HCID 312751,4-DioxaneHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 4885471HCID 4885471, compound

Reagents, catalysts & solvents 1

HCID 21966525Dioxane MethanolSolvent

Procedure

A mixture of 2-chloro-3-nitro-pyridine (5.0 g, 31.4 mmol), (4-amino-phenyl)-acetic acid (4.75 g 31.4 mmol), and a 4 N solution of HCl in dioxane (7.85 mL, 31.4 mmol) in MeOH/dioxane (100 mL; 1:1, v/v) is stirred and refluxed for 30 h. (4-Amino-phenyl)-acetic acid (4.75 g 31.4 mmol) is added and the reaction mixture is stirred and refluxed for additional 18 h. 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 (Hexane/EtOAc, 85:15→60:40) provides the title compound as a red solid: ES-MS: 288.0 [M+H]+; tR=4.71 min (System 1); Rf=0.20 (Hexane/EtOAc, 4:1).

Workup

  1. additionis added
  2. stirringthe reaction mixture is stirred
  3. temperaturerefluxed for additional 18 h
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue is dissolved in EtOAc
  6. washwashed with a saturated aqueous solution of NaHCO3
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification of the crude product by silica gel column chromatography (Hexane/EtOAc, 85:15→60:40)

Sources & evidence

ORD record
ord-8e7c20863c53491b8d2063c039336587
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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