N-(3-Benzyloxy-4-nitrobenzyl)-N-methylbenzenesulfonamide → N-(4-Amino-3-benzyloxybenzyl)-N-methylbenzenesulfonamide

HRID 660646Notes

Reaction equation

HRID 660646 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[N+:27]([O-])=O)[CH2:12][N:13]([CH3:23])[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.[Pt]=O>[NH2:27][C:26]1[CH:25]=[CH:24][C:11]([CH2:12][N:13]([CH3:23])[S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])=[CH:10][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 68840966N-(3-Benzyloxy-4-nitrobenzyl)-N-methylbenzenesulfonamide

Product 1

HCID 68839024N-(4-Amino-3-benzyloxybenzyl)-N-methylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)Catalyst3×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of N-(3-Benzyloxy-4-nitrobenzyl)-N-methylbenzenesulfonamide (1.09 g, 2.643 mmol) in EtOAc is added platinum oxide (60 mg). The reaction is placed under an atmosphere of H2 and stirred at RT for 50 min. Additional platinum oxide is added (60 mg) and the reaction is stirred under an atmosphere of H2 at RT for an additional 50 min. During this time, the reaction changes from a greenish brown slurry to a black slurry. The slurry is filtered through Celite to remove the catalyst and the filter cake is washed with several portions of EtOAc. The filtrate and washings are combined, and concentrated under vacuum to afford an orange oil. LC/MS shows a 1:1 mixture of starting material and product. The orange oil is re-dissolved in. EtOAc, slurried with platinum oxide (150 mg) and stirred under an atmosphere of H2 at room temperature for 1.5 h. The reaction mixture is filtered through Celite and the filter cake is washed with EtOAc. The filtrate is concentrated to afford the title compound: (M+1)+=383.

Workup

  1. stirringthe reaction is stirred under an atmosphere of H2 at RT for an additional 50 min
  2. customDuring this time, the reaction changes from a greenish brown slurry to a black slurry
  3. filtrationThe slurry is filtered through Celite
  4. customto remove the catalyst
  5. washthe filter cake is washed with several portions of EtOAc
  6. concentrationconcentrated under vacuum
  7. customto afford an orange oil
  8. additiona 1:1 mixture of starting material and product
  9. dissolutionThe orange oil is re-dissolved in
  10. stirringstirred under an atmosphere of H2 at room temperature for 1.5 h
  11. filtrationThe reaction mixture is filtered through Celite
  12. washthe filter cake is washed with EtOAc
  13. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-06eb11a5f8bc4748af93f457eeddae5c
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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