Hydrochloric Acid → 3-Amino-4,5-diethoxycarbonyl-2-phenyl-6-sulfopyridine

HRID 37511Notes

Reaction equation

C(OC([C:6]1([N+:27]([O-])=O)[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:9]([S:17]([OH:20])(=[O:19])=[O:18])=[N:8][CH:7]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O)C.Cl>C(O)C>[NH2:27][C:6]1[C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:8][C:9]([S:17]([OH:20])(=[O:18])=[O:19])=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 0.34 g of 3,4-diethoxycarbonyl-3-nitro-2-phenyl-6-sulfopyridine, 0.41 g of reduced iron and 7 ml of ethanol was heated to 60° C., and then 0.5 ml of conc. hydrochloric acid was added. The mixture was heated under reflux for 20 minutes. After the reaction mixture was concentrated to dryness, the residue was subjected to silica gel column chromatography (eluent:chloroform/methanol 5:1), to give 0.24 g of the title compound as pale yellow crystals.

Workup

temperatureThe mixture was heated
temperatureunder reflux for 20 minutes
concentrationAfter the reaction mixture was concentrated to dryness

Sources & evidence

ORD record: ord-a0ae2db61f414b338b9f80a607d7bf72
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420275

Reaction notes

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