2-Methyl-6-nitroaniline → HCID 178424004, compound

HRID 1789198Notes

Reaction equation

HRID 1789198 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[C:3]=1[NH2:4].[H][H].[OH-].[K+].C(O[C:19]([S-])=[S:20])C.[K+]>Cl.O1CCCC1.[Pd].C(O)C.O.CO>[SH:20][C:19]1[NH:4][C:3]2[C:2]([CH3:1])=[CH:8][CH:7]=[CH:6][C:5]=2[N:9]=1

Participants

11

Reactant 4

HCID 112982-Methyl-6-nitroanilineHCID 14797Potassium HydroxideHCID 2735045Potassium ethylxanthateHCID 178418361HCID 178418361, compound

Product 1

HCID 178424004HCID 178424004, compoundYield 29%

Reagents, catalysts & solvents 6

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 20 g (0.13 mole) of 2-methyl-6-nitroaniline in 22.9 ml of concentrated aqueous hydrochloric acid, 200 ml of tetrahydrofuran, and 350 ml of methanol was hydrogenated at room temperature using 25 p.s.i. of hydrogen gas over 2.0 g of 5% palladium on carbon. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in 150 ml of ethanol and neutralized with 17.2 g (0.26 mole) of potassium hydroxide dissolved in 30 ml of water. Potassium ethylxanthate (23 g, 0.155 mole) was added and the mixture was heated at reflux for 18 hours. Upon cooling, a solid was collected, washed with water, and air dried to yield 6.2 g of 2-mercapto-4-methylbenzimidazole, as confirmed by the nmr and infrared spectra. The title compound (987 mg) was prepared by the method of Example 6 using 8-hydroxymethylimidazo[1,2-a]pyridine as the hydrochloride salt (700 mg, 3.8 mmole) and using 655 mg (4.0 mmole) of 2-mercapto-4-methylbenzimidazole instead of 2-mercapto-5-methoxybenzimidazole. Structure assignment was supported by the nmr and infrared spectra.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. temperaturethe mixture was heated
  5. temperatureat reflux for 18 hours
  6. temperatureUpon cooling
  7. customa solid was collected
  8. washwashed with water, and air
  9. customdried

Sources & evidence

ORD record
ord-3c20324bed6f42eb896131d2c2e708b2
Source dataset
uspto-grants-1987_08
Patent number
US04687775

Reaction notes

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