Sulfuric Acid → HCID 23717813, compound

HRID 1978137Notes

Reaction equation

HRID 1978137 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C:6]1[C:15]2[C:10](=[C:11]([N+:16]([O-])=O)[CH:12]=[CH:13][CH:14]=2)[C:9]([S:19]([OH:22])(=[O:21])=[O:20])=[CH:8][CH:7]=1)=[O:4].S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+:32].[Na+]>O.[Fe]>[CH3:1][O:2][C:3]([CH2:5][C:6]1[C:15]2[C:10](=[C:11]([NH2:16])[CH:12]=[CH:13][CH:14]=2)[C:9]([S:19]([O-:22])(=[O:21])=[O:20])=[CH:8][CH:7]=1)=[O:4].[Na+:32]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 21713582HCID 21713582, compound

Product 1

HCID 23717813HCID 23717813, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Procedure

1-(methoxycarbonylmethyl)-5-nitro-4-naphthalene sulfonic acid (2 g, 6.15 mmol) was dissolved in water (20 mL), containing 0.5 mL concentrated sulfuric acid, and was added dropwise over 5 minutes to a refluxing suspension of iron (4 g, 71.6 mmol) in water (100 mL). After refluxing for one hour, the dark mixture was cooled to room temperature, made basic with sodium carbonate, and concentrated to approximately 30 mL. The residual mixture was placed on a CG-161 AMBERCHROM resin column (2.5×30 cm). The column was washed with water (200 mL), 10% MeCN/H2O(200 mL), and 25% MeCN/H2O (400 mL), collecting 25 mL fractions. Fractions 21-28 were combined and evaporated to give the title compound as a dark solid (0.675 g).

Workup

  1. temperatureAfter refluxing for one hour
  2. concentrationconcentrated to approximately 30 mL
  3. washThe column was washed with water (200 mL), 10% MeCN/H2O(200 mL), and 25% MeCN/H2O (400 mL)
  4. customcollecting 25 mL fractions
  5. customevaporated

Sources & evidence

ORD record
ord-da96dd3cf95e4faca3712f078f78320f
Source dataset
uspto-grants-2001_05
Patent number
US06235898B1

Reaction notes

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