Water → 2-(4-Ethoxyphenyl)-3-methyl-3H-naphtho[1,2-d]imidazole

HRID 1903177Notes

Reaction equation

HRID 1903177 reaction equation
[CH3:1][NH:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[N:13]=O.[CH2:15]([O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1)[CH3:16].O>C1(C)C=CC=CC=1.[Pd]>[CH3:1][N:2]1[C:3]2[CH:12]=[CH:11][C:10]3[C:5]([C:4]=2[N:13]=[C:22]1[C:21]1[CH:24]=[CH:25][C:18]([O:17][CH2:15][CH3:16])=[CH:19][CH:20]=1)=[CH:6][CH:7]=[CH:8][CH:9]=3

Participants

6

Reactant 3

HCID 962WaterHCID 248344-EthoxybenzaldehydeHCID 15562122HCID 15562122, compound

Product 1

HCID 132744142-(4-Ethoxyphenyl)-3-methyl-3H-naphtho[1,2-d]imidazole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent2×

Procedure

A solution of 11.16 g (0.06 mole) of 2-methylamino-1-nitrosonaphthalene in 800 cc of toluene is hydrogenated at room temperature and at the atmospheric pressure in the presence of 3 g of Palladium-on-carbon. After one hour, when the theoretical amount of hydrogen has been consumed, 9 cc (0.06 mole) of 4-ethoxy benzaldehyde are added and the obtained reaction mixture is heated to the reflux temperature under an inert atmosphere for about 3 hours. The water which forms during the reaction distillates as binary azeotrope with toluene and is separated through a Dean-Stark apparatus. Then further 1.5 g of 5% Palladium-on-carbon are added and reflux is prolonged for two additional hours. Filtration of the hot solution followed by concentration of the filtrate to dryness under vacuum affords a residue which has been purified by cristallization from ethyl acetate. Yield 14.5 g (80%) M.p. 138°-9° C.

Workup

  1. customwhen the theoretical amount of hydrogen has been consumed
  2. customthe obtained reaction mixture
  3. temperatureis heated to the reflux temperature under an inert atmosphere for about 3 hours
  4. customis separated through a Dean-Stark apparatus
  5. additionThen further 1.5 g of 5% Palladium-on-carbon are added
  6. temperaturereflux
  7. filtrationFiltration of the hot solution
  8. customaffords a residue which
  9. customhas been purified by cristallization from ethyl acetate

Sources & evidence

ORD record
ord-ee16ba790f2942a4b2d34905ff543609
Source dataset
uspto-grants-1984_03
Patent number
US04435417

Reaction notes

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