Hydrochloric Acid → 3-[2-(tert-Butoxycarbonyl)hydrazinyl]benzoic acid

HRID 1596512Notes

Reaction equation

HRID 1596512 reaction equation
[C:1]([O:5][C:6]([NH:8][NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([O:18]C)=[O:17])[CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].Cl>O1CCOCC1>[C:1]([O:5][C:6]([NH:8][NH:9][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=1)[C:16]([OH:18])=[O:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 21701824HCID 21701824, compound

Product 1

HCID 217018073-[2-(tert-Butoxycarbonyl)hydrazinyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

The 4.68 g of unpurified 1-tert-butoxycarbonyl-2-(3-methoxycarbonylphenyl)hydrazine was dissolved in 75 ml of 1,4-dioxane, and 25 ml of aqueous 3N potassium hydroxide solution was added to the solution, followed by heating the mixture at reflux for one hour. The reaction mixture was cooled to 0° C., and about 25 ml of 3N hydrochloric acid was added to make the reaction mixture acidic. The mixture was subjected to salting out and the resultant was extracted with ethyl acetate (2×50 ml). The organic layers were combined, dried and concentrated to obtain 4.40 g of unpurified captioned compound. NMR (90 MHz, CDCl3) δ1.47 (9H, s), 5.5-6.4 (2H, br s, OH, NH), 6.60 (1H, m, NH), 7.05 (1H, m), 7.32 (1H, br dd, J=8, 8 Hz), 7.50-7.70 (2H, m).

Workup

  1. temperatureby heating the mixture
  2. temperatureat reflux for one hour
  3. extractionthe resultant was extracted with ethyl acetate (2×50 ml)
  4. customdried
  5. concentrationconcentrated
  6. customto obtain 4.40 g

Sources & evidence

ORD record
ord-d1a554e3335440e1b9b4f1986de1acd8
Source dataset
uspto-grants-2001_09
Patent number
US06291470B1

Reaction notes

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