1-Naphthalenemethanamine → HCID 178450791, compound

HRID 1595323Notes

Reaction equation

HRID 1595323 reaction equation
O[N:2]=[C:3]([C:11](=O)[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[C:19]1([CH2:29][NH2:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[C:19]1([C:29]2[NH:30][C:11]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[C:3]([C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[N:2]=2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 83551-NaphthalenemethanamineHCID 178451310HCID 178451310, compound

Product 1

HCID 178450791HCID 178450791, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl 2-hydroxyimino-3-oxo-3-(4-pyridyl)propionate (5.0 g) and 1-naphthylmethylamine (3.5 g) were dissolved in toluene (60 ml). The mixture was refluxed under heating for 3 hr while dehydrating with Dean-stark trap. After cooling, the precipitated crystals were collected by filtration and dried to give tert-butyl 2-(1-naphthyl)-5-(4-pyridyl)imidazole-4-carboxylate (1.3 g), melting point 184-190° C.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 3 hr
  3. customwhile dehydrating with Dean-stark trap
  4. temperatureAfter cooling
  5. filtrationthe precipitated crystals were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-1fac82971a3c4260a168c4084530d8cb
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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