Hydrochloric Acid → HCID 67021390, compound

HRID 1660983Notes

Reaction equation

HRID 1660983 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)=[O:6])[CH3:2].Cl[C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=1.Cl>C(O)C.O1CCOCC1>[CH2:1]([O:3][C:4](=[O:14])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:9][CH:8]=1)=[O:6])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 796132-Chloro-3-nitropyridineHCID 20525885HCID 20525885, compound

Product 1

HCID 67021390HCID 67021390, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of (4-amino-phenyl)-oxo-acetic acid ethyl ester (347 mg, 1.8 mmol), 2-chloro-3-nitropyridine (294 mg, 1.8 mmol) and 4M HCl in dioxane (0.45 mL, 1.8 mmol) in ethanol (4 mL) is refluxed for 14 h. An additional 0.45 mL of 4M HCl in dioxane is added and the mixture refluxed for 5 h. The reaction mixture is cooled down to room temperature and the resulting precipitate is filtered off. [4-(3-Nitro-pyridin-2-ylamino)-phenyl]oxo-acetic acid ethyl ester is obtained as an orange solid. Title compound: ES-MS: 315.99 [M+H]+; tR=1.7 min (System 2).

Workup

  1. temperatureis refluxed for 14 h
  2. temperaturethe mixture refluxed for 5 h
  3. filtrationthe resulting precipitate is filtered off

Sources & evidence

ORD record
ord-f6896a7c0c7141a080a192d6423176b1
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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