HCID 19027052, compound → HCID 19027059, compound

HRID 1090083Notes

Reaction equation

HRID 1090083 reaction equation
[N+:1]([C:4]1[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[C:7]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Ni]>[NH2:1][C:4]1[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[C:7]([S:14]([NH2:17])(=[O:15])=[O:16])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 19027052HCID 19027052, compound

Product 1

HCID 19027059HCID 19027059, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1,2,3,4-tetrahydro-8-nitro-5-naphthalenesulfonamide (3.1 g, 12 mmol) in 150 ml of ethanol was hydrogenated at room temperature and atmospheric pressure over Raney-Ni. After the theoretical absorption, the reaction mixture was filtered and concentrated to dryness to give 2.6 g (95%) of the title compound. M.p. 216°-219° C. (ethanol); 1H-NMR (DMSO-d6): 1.50-1.93 (m, 4H, 2CH2), 2.17-2.57 (m, 2H, CH2), 2.83-3.17 (m, 2H, CH2), 5.29 (broad s, 2H, NH2), 6.38 (d,J=9Hz, 1H, ArH), 6.75 (broad s, 1H, SO ), 7.35 (d,J=9Hz, 1H, ArH).

Workup

  1. customwas hydrogenated at room temperature
  2. customAfter the theoretical absorption
  3. filtrationthe reaction mixture was filtered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a5c15c0d59de4b61baca4797a1d9483c
Source dataset
uspto-grants-1992_01
Patent number
US05081123

Reaction notes

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