Methane → HCID 13240334, compound

HRID 1649597Notes

Reaction equation

HRID 1649597 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][N:13]=[C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]([C:25]3[CH:26]([C:37]4[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[C:38]=4[Cl:44])[C:27]([C:33]([O:35][CH3:36])=[O:34])=[C:28]([CH3:32])[NH:29][C:30]=3[CH3:31])=[O:24])[CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H].C>C(O)C.[Ni].C(OCC)(=O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][N:13]=[C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]([C:25]3[CH:26]([C:37]4[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[C:38]=4[Cl:44])[C:27]([C:33]([O:35][CH3:36])=[O:34])=[C:28]([CH3:32])[NH:29][C:30]=3[CH3:31])=[O:24])[CH:11]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 297MethaneHCID 13240326HCID 13240326, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13240334HCID 13240334, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

12.86 g (20 mmole) of 1,4-dihydro-2,6-dimethyl-4-(2,3-dichlorophenyl)-3-methoxycarbonylpyridine-5-carboxylic acid 6-(5-p-nitrophenyl-3-pyrazolyloxy)hexyl ester (Example 60) was dissolved in 100 ml of ethanol, to which was added 5 ml of Raney nickel, and catalytic hydrogenation was effected at room temperature and atmospheric pressure, thereby 1350 ml (60 mmole) of hydrogen was absorbed. The Raney nickel was filtered off from the reaction mixture, and the filtrate was concentrated under reduced pressure to obtain a pale yellow oily residue. This residue was purified by chromatography on a silica gel column using a mixed solution of chloroform-methanol (the ratio by volume of 3:1) as an eluent, and the fractions containing the intended compound were concentrated under reduced pressure to obtain a pale yellow oily residue. This residue was dissolved in ethyl acetate, and after adding 5 g of activated charcoal, stirred well, and filtered. The filtrate was concentrated to dryness under reduced pressure to obtain 6.63 g (yield 54.0%) of the 1,4-dihydro-2,6-dimethyl-4 -(2,3-dichlorophenyl)-3-methoxycarbonylpyridine-5-carboxylic acid 6-(5-p-aminophenyl-3-pyrazolyloxy)hexyl ester as a pale yellow powder.

Workup

  1. customwas effected at room temperature
  2. filtrationThe Raney nickel was filtered off from the reaction mixture
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto obtain a pale yellow oily residue
  5. customThis residue was purified by chromatography on a silica gel column
  6. additionthe fractions containing the intended compound
  7. concentrationwere concentrated under reduced pressure
  8. customto obtain a pale yellow oily residue
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-54fb69a2668f4bb8a1112162025f16e0
Source dataset
uspto-grants-1983_11
Patent number
US04418197

Reaction notes

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