Hydrochloric Acid → HCID 22749250, compound
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
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 2.5 °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 ten to fifteen 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.
Workup
- additionare added
- temperatureto raise again to +5° C. within thirty minutes
- filtrationthis is filtered
- extractionextracted with chloroform
- washthe chloroformic phases are washed with water
- dry with materialdried over sodium sulfate
- customevaporated under reduced pressure
- dissolutionthe residue is dissolved in 30 c.c
- washthe formed precipitate is washed with ether
- customrecrystallized in xylene
Sources & evidence
- ORD record
- ord-47c8428f675846b380e0bd0f63e78b3a
- Source dataset
- uspto-grants-1979_02
- Patent number
- US04138572
Reaction notes
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