Hydrochloric Acid → HCID 67021570, compound

HRID 1010728Notes

Reaction equation

HRID 1010728 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.CCOC(C)=O>[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

7

Reactant 3

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

Product 1

HCID 67021570HCID 67021570, compound

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 21966525Dioxane MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1.5 g of 2-chloro-3-nitro-pyridine, 3.39 g of (4-amino-2-methyl-phenyl)-acetic acid methyl ester and 6.9 ml of an 4 N solution of HCl in dioxane in 30 ml of MeOH/dioxane (1:1, v/v) is stirred for 54 hours at 100° C. The mixture obtained is allowed to cool to rt and concentrated in vacuo. The concentrate obtained is dissolved in EtOAc, the mixture obtained is washed with a saturated aqueous solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The concentrate obtained is subjected to silica gel column chromatography. [2-Methyl-4-(3-nitro-pyridin-2-ylamino)-phenyl]-acetic acid methyl ester is obtained. ES-MS: 302.1 [M+H]+; tR=4.79 min (System 1); Rf=0.43 (CH2Cl2).

Workup

  1. customThe mixture obtained
  2. temperatureto cool to rt
  3. concentrationconcentrated in vacuo
  4. customThe concentrate obtained
  5. customthe mixture obtained
  6. washis washed with a saturated aqueous solution of NaHCO3
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe concentrate obtained

Sources & evidence

ORD record
ord-b2a2b93ed43b46c094ceb4d57832904a
Source dataset
uspto-grants-2011_07
Patent number
US07977338B2

Reaction notes

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