Hydrochloric Acid → Hydrochloric Acid

HRID 2350844Notes

Reaction equation

HRID 2350844 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([OH:14])=[C:6]([C:15]([NH:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[O:16])[CH:5]=1)([O-])=O.[ClH:23].[CH3:24]O>[Zn]>[NH2:1][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([OH:14])=[C:6]([C:15]([NH:17][CH2:18][CH2:19][C:20]([O:22][CH3:24])=[O:21])=[O:16])[CH:5]=1.[ClH:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 19847267HCID 19847267, compound

Product 2

HCID 313Hydrochloric AcidHCID 19847266HCID 19847266, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

An amount of 210 g of 4-nitro-2-(2-carboxyethylamino)carbonyl-1-naphthol was dissolved in 28 liters of methanol at 40° C. Into this solution was added 1,200 ml conc. hydrochloric acid, followed subsequently by portionwise addition of 430 g of zinc powder. After 30 minutes, zinc was removed and the solvent was removed by evaporation under reduced pressure. The residue was dissolved in 25 liters of ethyl acetate, washed with water and then dried over magnesium sulfate, followed by evaporation of the solvent, to give crystals. The crystals were washed with acetonitrile to obtain substantially pure desired product as hydrochloride. Yield was 75%. The product was confirmed by NMR, Mass spectra.

Workup

  1. customzinc was removed
  2. customthe solvent was removed by evaporation under reduced pressure
  3. dissolutionThe residue was dissolved in 25 liters of ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customfollowed by evaporation of the solvent
  7. customto give crystals
  8. washThe crystals were washed with acetonitrile

Sources & evidence

ORD record
ord-ef178c97612847afa1ccc14ea5be4fa1
Source dataset
uspto-grants-1989_10
Patent number
US04871655

Reaction notes

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