Hydrochloric Acid → HCID 19438632, compound

HRID 1733858Notes

Reaction equation

HRID 1733858 reaction equation
[CH3:1][N:2]([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.[N:18]([O-])=O.[Na+]>O.[Zn]>[CH2:15]([O:14][C:12]([CH2:11][CH2:10][CH2:9][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][C:6]([NH2:18])=[CH:5][CH:4]=1)=[O:13])[CH3:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 19438621HCID 19438621, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19438632HCID 19438632, compoundYield 38.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

Ethyl 4-(N-methylanilino)butyrate (J.C.S. Perkin I, 1972, 1803) (22 g) was dissolved by addition of conc. hydrochloric acid (60 ml) under ice-cooling. To the solution was added a solution of sodium nitrite (8 g) in water (10 ml) dropwise at 0° to 4° C. with vigorous stirring. The mixture was stirred at the same temperature for 30 minutes. Then zinc powder (30 g) was added at below 10° C. The resulting mixture was further stirred for 30 minutes at 15° C. The zinc was filtered off. The filtrate was made alkaline with sodium bicarbonate and then was extracted with ether. The ether layer was dried over anhydrous sodium sulfate and concentrated. The residue was subjected to column chromatography on silica gel and developed with ethyl acetate/hexane (1:1) to obtain N-ethoxycarbonylpropyl-N-methyl-p-phenylenediamine (9 g).

Workup

  1. temperaturecooling
  2. stirringThe resulting mixture was further stirred for 30 minutes at 15° C
  3. filtrationThe zinc was filtered off
  4. extractionwas extracted with ether
  5. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-93032645c88b42adb56349b95783a807
Source dataset
uspto-grants-1996_07
Patent number
US05532171

Reaction notes

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