Sulfuric Acid → HCID 21466980, compound

HRID 440123Notes

Reaction equation

HRID 440123 reaction equation
[C:1]([C:4]1([CH2:17][C:18]([OH:20])=[O:19])[C:9]2[CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=[CH:13][C:8]=2[O:7][CH2:6][CH2:5]1)([OH:3])=[O:2].S(=O)(=O)(O)O>[Pd].C(O)C>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]2[O:7][CH2:6][CH2:5][C:4]([C:1]([OH:3])=[O:2])([CH2:17][C:18]([OH:20])=[O:19])[C:9]=2[CH:10]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 21466970HCID 21466970, compound

Product 1

HCID 21466980HCID 21466980, compoundYield 73.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-carboxy-3,4-dihydro-6-nitro-2H-1-benzopyran-4-acetic acid (4.1 g, 14 mmol), 10% palladium on carbon (1.6 g) and sulfuric acid (1 mL) in ethanol is hydrogenated at 45 psi for 2 hours and filtered through diatomaceous earth. The filtrate is concentrated in vacuo to obtain the title product as a tan solid (2.6 g) which is identified by 1H and 13CNMR spectral analyses.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-026dd7fd92e64fdb96d7171a934412f3
Source dataset
uspto-grants-1996_05
Patent number
US05516918

Reaction notes

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