Acetic Acid → HCID 22388025, compound

HRID 1072804Notes

Reaction equation

HRID 1072804 reaction equation
[NH2:1][C:2]1[C:12]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.C(=O)([O-])O.[Na+].[C:28](O)(=O)[CH3:29]>>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[CH2:14][N:13]1[C:12]2[C:2](=[N:3][CH:4]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:11]=2)[N:1]=[C:28]1[CH3:29]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 22388290Ethyl 6-amino-5-[[(2,4-dichlorophenyl)methyl]amino]-3-pyridinecarboxylate

Product 1

HCID 22388025HCID 22388025, compoundYield 89.7%

Conditions

Temperature
100 °C

Procedure

A suspension of ethyl 6-amino5-(2,4-dichlorobenzylamino)nicotinate (300 mg) and acetic acid (132 mg) in polyphosphoric acid (6 g) was heated to 100° C. Two hours later, the reaction mixture was cooled and ice (5 g) was added. The mixture was neutralized with a saturated aqueous sodium hydrogencarbonate and extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous sulfate and filtrated. The filtrate was concentrated and the residue was crystallized from isopropyl ether to give the objective compound (288 mg) as pale-brown crystals.

Workup

  1. temperatureTwo hours later, the reaction mixture was cooled
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sulfate
  5. filtrationfiltrated
  6. concentrationThe filtrate was concentrated
  7. customthe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-14b91c145e6a492b93571004e046f1c0
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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