Acetic Acid → 2-Amino-3-cyclopentylbenzenesulphonic acid

HRID 727443Notes

Reaction equation

HRID 727443 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]2[CH2:12][CH2:11][CH:10]=[CH:9]2)=[CH:6][C:5](Br)=[CH:4][C:3]=1[S:14]([OH:17])(=[O:16])=[O:15].CO.C(O)(=O)C>[Pd].O>[NH2:1][C:2]1[C:7]([CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12]2)=[CH:6][CH:5]=[CH:4][C:3]=1[S:14]([OH:17])(=[O:15])=[O:16]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 189316652-Amino-5-bromo-3-cyclopent-2-en-1-ylbenzenesulphonic acid

Product 1

HCID 189193792-Amino-3-cyclopentylbenzenesulphonic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

9.6 g (30.3 mmol) of 2-amino-5-bromo-3-cyclopent-2-en-1-ylbenzenesulphonic acid are placed in a Parr apparatus and 1 g of 10% palladium-on-charcoal, 80 ml of methanol, 10 ml of acetic acid and 50 ml of water are added. The reaction medium is heated to 50° C. under a pressure of 0.35 MPa (50 psi). It is filtered through Celite, the filtrate is concentrated under reduced pressure and the residue thus obtained is crystallized from a methanol/pentane mixture.

Workup

  1. additionare added
  2. filtrationIt is filtered through Celite
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customthe residue thus obtained
  5. customis crystallized from a methanol/pentane mixture

Sources & evidence

ORD record
ord-681c74379cad406fbfa08d5e4203b346
Source dataset
uspto-grants-1998_01
Patent number
US05712393

Reaction notes

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