HCID 19098340, compound → 1-(4-Chlorobenzyl)-1-(4-methoxyphenyl)hydrazine hydrochloride

HRID 1975730Notes

Reaction equation

HRID 1975730 reaction equation
[N:1]([N:3]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)=O.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[ClH:19].[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:3]([C:4]2[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=2)[NH2:1])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 19098340HCID 19098340, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 189475691-(4-Chlorobenzyl)-1-(4-methoxyphenyl)hydrazine hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N-nitroso-N-(4-chlorobenzyl)-4-methoxyaniline (98.7 g; 357 mmol), prepared as above, in 1200 mL THF was cooled to 0° C. and 1230 mL of a 1M solution of diisobutylaluminum hydride in hexanes was added dropwise. The ice bath was removed and the reaction was heated at reflux overnight. The reaction was cooled to ambient temperature and poured into 10% aqueous HCl. The layers were separated and the aqueous was extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and then concentrated. The crude material was dissolved in 400 mL of 1:1 ethyl acetate, hexane and treated with HCl gas. The resultant solid was collected to yield 1-(4-chlorobenzyl)-1-(4-methoxyphenyl)-hydrazine hydrochloride which was used with no further purification.

Workup

  1. customThe ice bath was removed
  2. temperaturethe reaction was heated
  3. temperatureat reflux overnight
  4. temperatureThe reaction was cooled to ambient temperature
  5. additionpoured into 10% aqueous HCl
  6. customThe layers were separated
  7. extractionthe aqueous was extracted with ethyl acetate
  8. dry with materialThe combined extracts were dried over magnesium sulfate
  9. concentrationconcentrated
  10. dissolutionThe crude material was dissolved in 400 mL of 1:1 ethyl acetate
  11. additionhexane and treated with HCl gas
  12. customThe resultant solid was collected

Sources & evidence

ORD record
ord-aa0964694de8444c9cb3b3bc68099806
Source dataset
uspto-grants-1994_02
Patent number
US05288743

Reaction notes

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