Nitric Acid → HCID 20485272, compound
Reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[N:4]([CH3:6])[CH3:5].[N+]([O-])(O)=[O:13].C(=O)([O-])[O-].[Na+].[Na+].[N+](C1C(C)=C(C(C)=CC=1)N(C)C)([O-])=O>S(=O)(=O)(O)O.O>[OH:13][C:10]1[C:2]([CH3:1])=[C:3]([C:7]([CH3:11])=[CH:8][CH:9]=1)[N:4]([CH3:5])[CH3:6]Participants
Procedure
40 ml of 2,6-dimethyl-N,N-dimethylaniline was dissolved in 88 ml of concentrated sulfuric acid at a temperature below 15° C., followed by dropwise addition of 35 ml of concentrated nitric acid by maintaining the temperature below 15° C. Thereafter, the mixture was reacted for one hour, poured into cold water and then neutralized with sodium carbonate, whereby 3-nitro-2,6-dimethyl-N,N-dimethylaniline was precipitated in the form of crystals. The produced nitro compound was reduced, diazotized and then pyrolyzed to obtain 3-hydroxy-2,6-dimethyl-N,N-dimethylaniline. This phenol compound was dissolved in an alkaline solution and treated with excess dimethyl sulfate at 40°-45° C. The resulting 3-methoxy-2,6-dimethyl-N,N-dimethylaniline was dissolved in hydrochloric acid and then admixed with double molar amount of zinc chloride to precipitate a double salt. It was recrystallized from dilute hydrochloric acid to obtain the salt of formula V. M.p.: 162°-165° C., amount of zinc: 11.8% (calculated: 11.4%); infrared absorption spectra: 3100 cm-1, 1450 cm-1, 1260 cm-1, 1070 cm-1, 820 cm-1, 1600 cm-1 ; NMR (chemical shift): 3.4 ppm, 3.9 ppm, 2.4 ppm, 2.5 ppm, 7.1 ppm, 7.2 ppm, 7.0 ppm, 7.3 ppm.
Workup
- temperatureby maintaining the temperature below 15° C
- customThereafter, the mixture was reacted for one hour
- customwas precipitated in the form of crystals
Sources & evidence
- ORD record
- ord-a4ef265646cb47dab2969507cc150006
- Source dataset
- uspto-grants-1983_10
- Patent number
- US04409313
Reaction notes
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