Hydrochloric Acid → HCID 19870659, compound

HRID 329968Notes

Reaction equation

HRID 329968 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:13])=[O:12])=[CH:6][CH:5]=1)([O-])=O.[ClH:21]>C(OCC)(=O)C.C(O)C.[Pd]=O>[ClH:21].[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11]([O:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)(=[O:13])=[O:12])=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 13204062Phenyl (4-nitrophenyl)methanesulfonate

Product 1

HCID 19870659HCID 19870659, compound

Reagents, catalysts & solvents 3

HCID 5083724Palladium monoxideCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of phenyl 4-nitrobenzenemethanesulphonate (1.6 g) in ethyl acetate (200 ml) and concentrated hydrochloric acid (1 ml) was hydrogenated over prereduced 5% palladium oxide on charcoal (50% aqueous paste 0.4 g) in ethanol (10 ml) at atmospheric pressure and temperature. The catalyst was filtered off and the filtrate concentrated to give the title compound as a solid (1.55 g). A small sample (0.2 g) was crystallized from isopropyl acetate (10 ml) and a few drops of methanol to give analytically pure material (70 mg) m.p. 147°-148°.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-03c8d9dc65664e0f8a8d12aeb03352e5
Source dataset
uspto-grants-1990_01
Patent number
US04894387

Reaction notes

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