Hydrochloric Acid → HCID 22749250, compound

HRID 1414512Notes

Reaction equation

HRID 1414512 reaction equation
[C:1]([CH2:6][C:7]([N:9]([CH3:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-])=O)=[O:8])([O:3][CH2:4][CH3:5])=[O:2].Cl>[Zn].O>[C:1]([CH2:6][C:7]([N:9]([CH3:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16])=[O:8])([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 24976598HCID 24976598, compound

Product 1

HCID 22749250HCID 22749250, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

11 g of N-carbethoxy acetyl N-methyl o-nitro aniline are admixed with 16.2 g of powdered zinc, and 100 g of cracked ice are added, whilst agitating; 62 c.c. of concentrated hydrochloric acid, diluted with 250 c.c. of iced water, are then added, and this is cooled to -5°-10° C for 10 to 15 minutes; the temperature is allowed to raise again to + 5° C within thirty minutes, this is filtered, the filtrate is alkalinized with ammonium hydroxide and extracted with chloroform; the chloroformic phases are washed with water, dried over sodium sulfate and evaporated under reduced pressure; the residue is dissolved in 30 c.c. of xylene and the solution is kept overnight at -10° C; the formed precipitate is washed with ether and recrystallized in xylene, to obtain N-carbethoxy acetyl N-methyl o-phenylene diamine, melting at 63°-64° C. Analysis: C12H16N2O3 = 256.26; Calculated: C % 61.00; H % 6.83; N % 11.86; Found: 61.19; 6.98; 12.00.

Workup

  1. additionare added
  2. temperaturethis is cooled to -5°-10° C for 10 to 15 minutes
  3. filtrationthis is filtered
  4. extractionextracted with chloroform
  5. washthe chloroformic phases are washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. dissolutionthe residue is dissolved in 30 c.c
  9. washthe formed precipitate is washed with ether
  10. customrecrystallized in xylene

Sources & evidence

ORD record
ord-c793f2ff788a4574a4e19f34a2186865
Source dataset
uspto-grants-1977_01
Patent number
US04001408

Reaction notes

Loading…