Quinoline → HCID 53913170, compound

HRID 2166073Notes

Reaction equation

HRID 2166073 reaction equation
[N:1]1([CH:6]([C:10]2[CH:19]=[CH:18][C:13]3[N:14]([CH3:17])[N:15]=[N:16][C:12]=3[CH:11]=2)[C:7]#[C:8][CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1.N1C2C(=CC=CC=2)C=CC=1.C(OCC)(=O)C.[H][H]>[Pd].C(O)C>[N:1]1([CH:6]([C:10]2[CH:19]=[CH:18][C:13]3[N:14]([CH3:17])[N:15]=[N:16][C:12]=3[CH:11]=2)[CH:7]=[CH:8][CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 7047QuinolineHCID 8857Ethyl AcetateHCID 15097100HCID 15097100, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53913170HCID 53913170, compoundYield 19.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7 parts of 5-[1-(1H-imidazol-1-yl)-2-butynyl]-1-methyl-1H-benzotriazole, 0.1 parts of quinoline, 54 parts of ethyl acetate and 32 parts of ethanol was hydrogenated at 931.00 Pa and at room temperature with 0.3 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off over diatomaceous earth and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of dichloromethane and 1,1'-oxybisethane. The product was filtered off and dried, yielding 1.4 parts (19.7%) of 5-[1-(1H-imidazol-1-yl)-2-butenyl]-1-methyl-1H-benzotriazole; mp. 104° C. (compound 240).

Workup

  1. filtrationthe catalyst was filtered off over diatomaceous earth
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography over silica gel using
  4. additiona mixture of dichloromethane and methanol (95:5 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. customThe residue was crystallized from a mixture of dichloromethane and 1,1'-oxybisethane
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-045d8f12a16f4b56869628e1f3cf0218
Source dataset
uspto-grants-1990_07
Patent number
US04943574

Reaction notes

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