Hydrochloric Acid → HCID 19086258, compound

HRID 1033015Notes

Reaction equation

HRID 1033015 reaction equation
C[O:2][C:3]1[C:8]([CH2:9][NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[CH:7][C:6]([CH2:21][CH3:22])=[C:5]([CH3:23])[N:4]=1.Cl.N1C=CC=CC=1.Cl>O>[C:11]1([NH:10][CH2:9][C:8]2[C:3](=[O:2])[NH:4][C:5]([CH3:23])=[C:6]([CH2:21][CH3:22])[CH:7]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10176127Pyridinium chlorideHCID 19086259HCID 19086259, compound

Product 1

HCID 19086258HCID 19086258, compoundYield 15.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-methoxy-3-{[1-naphthylamino]-methyl}-5-ethyl-6-methylpyridine (125 mg, 0.41 mmol) and pyridine hydrochloride (500 mg, 4.3 mmol) was warmed at 145°-160° C. for 20 minutes. The reaction mixture was then cooled, water added, and the mixture made acidic with dilute aqueous hydrochloride acid. The product was then extracted into chloroform. Chloroform extracts were concentrated and the residue flash chromatographed on silica gel eluting with 5% methanol/95% chloroform. Appropriate fractions were combined and evaporated. The residue was triturated with diethyl ether to give 18.9 mg (15%) of product, m.p. 165°-167° C.

Workup

  1. temperaturewas warmed at 145°-160° C. for 20 minutes
  2. temperatureThe reaction mixture was then cooled
  3. extractionThe product was then extracted into chloroform
  4. concentrationChloroform extracts were concentrated
  5. customthe residue flash chromatographed on silica gel eluting with 5% methanol/95% chloroform
  6. customevaporated
  7. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-c734faef926f4ef5bddd16c3b82bdef1
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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