Methanol → HCID 21717349, compound

HRID 1386063Notes

Reaction equation

HRID 1386063 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:9]([CH3:13])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:16]=1[CH:17]=O.CO.[OH-].[Na+]>C(OCC)(=O)C.[Cl-].[Cl-].[Zn+2].CCOCC.O>[Cl:8][C:6]1[CH:7]=[C:2]([NH:1][CH2:17][C:16]2[C:19]([CH3:23])=[CH:20][CH:21]=[CH:22][C:15]=2[CH3:14])[C:3]2[N:4]([C:9]([CH3:13])=[C:10]([CH3:12])[N:11]=2)[CH:5]=1

Participants

9

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 5838412,6-Dimethylbenzaldehyde2×HCID 21717323HCID 21717323, compound

Product 1

HCID 21717349HCID 21717349, compoundYield 36.3%

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalyst2×HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8-amino-6-chloro-2,3-dimethylimidazo[1,2-a]pyridine (0.894 g, 4.57 mmol), 2,6-dimethylbenzaldehyde (0.77 g, 5.7 mmol), ZnCl2 (1.08 g, 7.92 mmol), NaB(CN)H3 (0.36 g, 5.7 mmol) and MeOH (35 ml) was refluxed for 3.5 h. More 2,6-dimethylbenzaldehyde (0.25 g in 4 ml MeOH), ZnCl2 (0.55 g) and NaB(CN)H3 (0.35 g) were added. The reaction mixture was refluxed for additional 4 h. Subsequent workup by addition of 1 M NaOH (150 ml), and water (50 ml), followed by extraction of the mixture with CH2Cl2, drying, and evaporation of solvent gave a solid residue. The crude product dissolved in ethyl acetate and ether was added. Filtration and evaporation of solvent gave a residue which was recrystallized from ethyl acetate to give 0.52 g product.

Workup

  1. temperaturewas refluxed for 3.5 h
  2. temperatureThe reaction mixture was refluxed for additional 4 h
  3. extractionfollowed by extraction of the mixture with CH2Cl2
  4. customdrying
  5. customevaporation of solvent
  6. customgave a solid residue
  7. filtrationFiltration and evaporation of solvent
  8. customgave a residue which
  9. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2a49c057d1a04ee4a8f79605c339588f
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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