4-[(4-Methylphenyl)sulfonyl]-9-nitro-3,4,5,6-tetrahydro-2H-1,7,4-benzodioxazonine → 9-Amino-4-[(4-methylphenyl)sulfonyl]-3,4,5,6-tetrahydro-2H-1,7,4-benzodioxazonine

HRID 1089546Notes

Reaction equation

HRID 1089546 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:19][CH2:18][O:17][C:16]3[CH:20]=[CH:21][C:22]([N+:24]([O-])=O)=[CH:23][C:15]=3[O:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H][H]>[OH-].[OH-].[Pd+2].C(OCC)(=O)C>[NH2:24][C:22]1[CH:21]=[CH:20][C:16]2[O:17][CH2:18][CH2:19][N:11]([S:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)(=[O:10])=[O:9])[CH2:12][CH2:13][O:14][C:15]=2[CH:23]=1

Participants

5

Reactant 2

HCID 148563554-[(4-Methylphenyl)sulfonyl]-9-nitro-3,4,5,6-tetrahydro-2H-1,7,4-benzodioxazonineHCID 178418361HCID 178418361, compound

Product 1

HCID 148563569-Amino-4-[(4-methylphenyl)sulfonyl]-3,4,5,6-tetrahydro-2H-1,7,4-benzodioxazonine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To ethyl acetate (1 L) add 4-[(4-methylphenyl)sulfonyl]-9-nitro-3,4,5,6-tetrahydro-2H-1,7,4-benzodioxazonine (7.5 g, 20 mmol) and Pd(OH)2 on carbon (1.0 g). Place the reaction mixture on a Parr hydrogenator and shake at 50 psi of hydrogen. Monitor the progress of the reaction by thin-layer chromatography. Upon completion remove the catalyst by suction filtration through celite. Remove the solvent in vacuo to obtain the title compound.

Workup

  1. customMonitor the progress of the reaction by thin-layer chromatography
  2. customUpon completion remove the catalyst
  3. filtrationby suction filtration through celite
  4. customRemove the solvent in vacuo

Sources & evidence

ORD record
ord-5828120458954defa077e1d16a470e5b
Source dataset
uspto-grants-1990_10
Patent number
US04966967

Reaction notes

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