Hydrochloric Acid → 2-methyl-4-(methyloxy)-5-nitroaniline HCl salt

HRID 1014404Notes

Reaction equation

HRID 1014404 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[NH:13]C(=O)C.O1CCOCC1.[ClH:23]>CO>[ClH:23].[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[NH2:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 21260362N-(4-Methoxy-2-methyl-5-nitrophenyl)acetamide

Product 1

HCID 673166642-methyl-4-(methyloxy)-5-nitroaniline HCl salt

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A slurry of N-[2-methyl-4-(methyloxy)-5-nitrophenyl]acetamide (1 g, 4.46 mmol) in methanol (20 ml) and 4M HCl in dioxane (8.92 ml, 35.7 mmol) was heated at 60° C. for 18 h. The reaction mixture was cooled in an ice bath and solids were filtered and washed with cold methanol to afford 2-methyl-4-(methyloxy)-5-nitroaniline HCl salt (0.516 g, 2.36 mmol) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.38 (s, 3 H) 3.91 (s, 3 H) 7.31 (s, 1 H) 7.87 (s, 1 H) 9.39 (br. s., 2 H)

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. filtrationsolids were filtered
  3. washwashed with cold methanol

Sources & evidence

ORD record
ord-143d0ebdbeb44b02bc981257aed599bc
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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