Dichloromethane → 1,8-Naphthyridine

HRID 1786359Notes

Reaction equation

HRID 1786359 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].Cl[C:13]1[CH:18]=CC=C[CH:14]=1.C(Cl)Cl>CO>[N:3]1[C:2]2[C:7](=[CH:14][CH:13]=[CH:18][N:1]=2)[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7964ChlorobenzeneHCID 104392-AminopyridineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1360691,8-Naphthyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of aminopyridine (1.12 g, 5.833 mmol) and AlCl3 (3.11 g, 0.023 mol) was added chlorobenzene (10.0 mL) in a sealed vessel under Ar. The reaction was sealed and heated to 120° C. for 12 h. The reaction mixture was cooled to RT and the mixture was poured over ice/HCl mixture and extracted with EtOAc (3×50.0 mL). The aqueous layer was neutralized via addition of solid NaHCO3 and extracted with EtOAc (5×50 mL). Combined organic layers were dried over Na2SO4 and evaporated to dryness to yield crude compound. Chromatography (Silica gel, CH2Cl2:MeOH, 99:1) yielded pure naphthyridin.

Workup

  1. customThe reaction was sealed
  2. temperatureThe reaction mixture was cooled to RT
  3. extractionextracted with EtOAc (3×50.0 mL)
  4. additionThe aqueous layer was neutralized via addition of solid NaHCO3
  5. extractionextracted with EtOAc (5×50 mL)
  6. dry with materialCombined organic layers were dried over Na2SO4
  7. customevaporated to dryness
  8. customto yield crude compound

Sources & evidence

ORD record
ord-e687a9f79e8a489cbcb5bdf12ac42fc7
Source dataset
uspto-grants-2009_03
Patent number
US07507748B2

Reaction notes

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