Hydrochloric Acid → HCID 22749250, compound

HRID 1287212Notes

Reaction equation

HRID 1287212 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]>[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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 24976598HCID 24976598, compound

Product 1

HCID 22749250HCID 22749250, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

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 cc. of concentrated hydrochloric acid, diluted with 250 cc. of ice 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 30 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 cc. 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.

Workup

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

Sources & evidence

ORD record
ord-29e4c0dc35e14bc2a464a829e9c1fcdf
Source dataset
uspto-grants-1976_10
Patent number
US03984398

Reaction notes

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