Hydrochloric Acid → Ethyl alpha-amino-9H-thioxanthene-9-acetate hydrochloride

HRID 258192Notes

Reaction equation

HRID 258192 reaction equation
[N+:1]([CH:4]([CH:10]1[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:17][C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:5]([O:7][CH2:8][CH3:9])=[O:6])([O-])=O.[ClH:24]>C(O)C.[Pd]>[ClH:24].[NH2:1][CH:4]([CH:10]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=2[S:17][C:18]2[C:23]1=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15290759Ethyl alpha-nitro-9H-thioxanthene-9-acetate

Product 1

HCID 67804420Ethyl alpha-amino-9H-thioxanthene-9-acetate hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl α-nitro-9H-thioxanthene-9-acetate (4.4 g, 13.4 mmol) is hydrogenated in 200 mL of ethanol and 13.5 mL of concentrated hydrochloric acid with 1.0 g of 20% palladium on carbon (51 psi, 28 hours). The filtered solution is stripped of solvent and the residual solid washed with dichloromethane, dried at 45° C./2 mm Hg. This gives 3.66 g of the title compound; mp 238°-240° C. An additional crop (0.41 g) is obtained after cooling the mother liquor; mp 233°-236° C.

Workup

  1. washthe residual solid washed with dichloromethane
  2. customdried at 45° C./2 mm Hg
  3. customAn additional crop (0.41 g) is obtained
  4. temperatureafter cooling the mother liquor

Sources & evidence

ORD record
ord-ee4a66becd9e443bb7548d2b933959c3
Source dataset
uspto-grants-1993_11
Patent number
US05264577

Reaction notes

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