Water → 3-Amino-1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethylbenzene

HRID 850175Notes

Reaction equation

HRID 850175 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]([N+:27]([O-])=O)[C:21]=1[CH3:30])([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.[Cl-].[NH4+].O>C(O)C.[Fe]>[NH2:27][C:22]1[C:21]([CH3:30])=[C:20]([CH2:19][O:18][Si:1]([C:14]([CH3:16])([CH3:15])[CH3:17])([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:25]([CH3:26])=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 107645571-(Tert-butyldiphenylsilyloxymethyl)-2,6-dimethyl-3-nitrobenzene

Product 1

HCID 107391063-Amino-1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethylbenzeneYield 109.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 702EthanolSolvent

Procedure

To a suspension of 1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethyl-3-nitrobenzene (42 g) and ammonium chloride (4.2 g) in ethanol (378 ml)-water (42 ml) was added iron (7.0 g), and the mixture was refluxed for 6 hours, during which iron (7.0 g) was added thereto twice. Insoluble materials were filtered off, and the filtrate was concentrated. To the residue was added water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated to give 3-amino-1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethylbenzene (42.8 g) as pale yellow oil.

Workup

  1. additionwas added
  2. filtrationInsoluble materials were filtered off
  3. concentrationthe filtrate was concentrated
  4. additionTo the residue was added water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-96c31039bf544a0992b6db24ccc2d781
Source dataset
uspto-grants-2000_01
Patent number
US06015818

Reaction notes

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