Hydrazine hydrate (1:1) → 3-(Tert-butyldiphenylsilyloxymethyl)-2,4-dichloroaniline

HRID 636474

Reaction equation

HRID 636474 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[C:22]([N+:27]([O-])=O)[C:21]=1[Cl:30])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>CO.O>[NH2:27][C:22]1[C:21]([Cl:30])=[C:20]([CH2:19][O:18][Si:1]([C:14]([CH3:16])([CH3:15])[CH3:17])([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:25]([Cl:26])=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 117981851-(Tert-butyldiphenylsilyloxymethyl)-2,6-dichloro-3-nitrobenzene

Product 1

HCID 105987193-(Tert-butyldiphenylsilyloxymethyl)-2,4-dichloroanilineYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of 1-(tert-butyldiphenylsilyloxy-methyl)-2,6-dichloro-3-nitrobenzene (433 mg), ferric chloride hexahydrate (17.5 mg) and activated carbon (17.5 mg) in a mixture of methanol (2.78 ml) and water (0.69 ml) was added hydrazine monohydrate (0.135 ml) dropwise at 60-70° C. After the addition was finished, the mixture was refluxed for half an hour. The mixture was allowed to cool and filtered. The filtrate was concentrated in vacuo. The residue was extracted with dichloromethane and the organic phase was dried over anhydrous magnesium sulfate. After being filtered, the filtlate was concentrated in vacuo and the resulting residue was washed with n-hexane to give 3-amino-1-(tert-butyldiphenylsilyloxymethyl)-2,6-dichlorobenzene (348 mg) as a white mass.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed for half an hour
  3. temperatureto cool
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. extractionThe residue was extracted with dichloromethane
  7. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  8. filtrationAfter being filtered
  9. concentrationthe filtlate was concentrated in vacuo
  10. washthe resulting residue was washed with n-hexane

Sources & evidence

ORD record
ord-0cf490bdb91e4ca68f1362a6224b60c5
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Linked notes

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