HCID 68809407, compound → HCID 68947259, compound

HRID 2180916Notes

Reaction equation

HRID 2180916 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([CH2:10][Cl:11])[CH:7]=[CH:6][C:5]=1[S:12][C:13]1[C:14](=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:15]([O:17][CH3:18])=[O:16])([O-])=O>CO.[Ni].C(Cl)(Cl)Cl>[NH2:1][C:4]1[CH:9]=[C:8]([CH2:10][Cl:11])[CH:7]=[CH:6][C:5]=1[S:12][C:13]1[C:14](=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 1

HCID 68809407HCID 68809407, compound

Product 1

HCID 68947259HCID 68947259, compoundYield 95.4%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

A solution of 9.0 g (27.8 mmol) of methyl S-(2-nitro-4-chloromethylphenyl)thiosalicylate in 100 mL of methanol was hydrogenated over Raney nickel (1.12 g) at room temperature and 30 psi pressure with stirring for 17 hours. The residue obtained on evaporation of the methanol was dissolved in chloroform, filtered, dried over MgSO4, filtered, and concentrated in vacuo to provide methyl S-(2-amino-4-chloromethylphenyl)thiosalicylate as a white solid (8.16 g, 55.6%), 1H NMR (300 MHz, CDCl3) δ 4.00 (s, 3H, —OCH3), 4.40 (s, 2H, —NH2), 6.77 (dd, 1H, J=1.2 Hz), 6.79 (dd, 1H, J=2.1 Hz), 6.84 (dd, 1H, J=2.4 Hz), 7.15-7.20 (m, 1H), 7.28-7.34 (m, 1H), 7.40 (d, 1H, J=8.1 Hz), 8.006 (dd, 1H, J=1.5 Hz).

Workup

  1. filtrationfiltered
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7f2fed4f33964b768a2d1013abae7a7c
Source dataset
uspto-grants-2005_05
Patent number
US06890919B2

Reaction notes

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