Water → 3-Methyl-2-{4-[(propan-2-yl)oxy]phenyl}-3H-naphtho[1,2-d]imidazole

HRID 1759329Notes

Reaction equation

HRID 1759329 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.[CH3:15][CH:16]([O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)[CH3:17].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:23]1[C:22]1[CH:25]=[CH:26][C:19]([O:18][CH:16]([CH3:17])[CH3:15])=[CH:20][CH:21]=1)=[CH:6][CH:7]=[CH:8][CH:9]=3

Participants

6

Reactant 3

HCID 962WaterHCID 2500774-IsopropoxybenzaldehydeHCID 15562122HCID 15562122, compound

Product 1

HCID 140118333-Methyl-2-{4-[(propan-2-yl)oxy]phenyl}-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, 0.06 mole of 4-(1-methylethoxy)-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 ether. M.p. 144°-5° 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 ether

Sources & evidence

ORD record
ord-e2727fa7fabe4c66a103da8f9362d9e2
Source dataset
uspto-grants-1982_07
Patent number
US04340607

Reaction notes

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