3-Pyridinemethanamine → HCID 14518368, compound

HRID 1723112Notes

Reaction equation

HRID 1723112 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][NH2:24])[CH:18]=1>C(O)C>[N:9]1([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([NH:24][CH2:23][C:19]3[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=3)=[C:3]([N+:14]([O-:16])=[O:15])[CH:4]=2)[CH:13]=[CH:12][N:11]=[CH:10]1

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 14990940HCID 14990940, compound

Product 1

HCID 14518368HCID 14518368, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(a-3) A mixture of 4.4 parts of 1-[(4-fluoro-3-nitrophenyl)methyl]-1H-imidazole, 4.33 parts of 3-pyridinemethanamine and 80 parts of absolute ethanol was stirred for 4 hours at reflux temperature. The reaction mixture was evaporated. 50 Parts of water were added to the residue. The product was extracted twice with 130 parts of trichloromethane. The combined trichloromethane layers were dried, filtered and evaporated. The residue was crystallized from 48 parts of 2-propanol. The product was filtered off and dried, yielding 5.1 parts (82%) of N-[4-(1H-imidazol-1-ylmethyl)-2-nitrophenyl]-3-pyridinemethanamine; mp. 171.0° C. (int. 71).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. addition50 Parts of water were added to the residue
  4. extractionThe product was extracted twice with 130 parts of trichloromethane
  5. dry with materialThe combined trichloromethane layers were dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from 48 parts of 2-propanol
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-c9cc5607ce1147c9b3579884467ba095
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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