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Hydrochloric Acid → alpha-((Aminocarbonyl)amino)-4-hydroxybenzeneacetic acid

HRID 892946
Notes
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Reaction equation

HRID 892946 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:12][C:11](=[O:13])[NH:10][C:9]2=[O:14])=[CH:4][CH:3]=1.S(O)(O)(=O)=[O:16].NO.[OH-].[Na+].Cl>[O-]S(S([O-])=O)=O.[Na+].[Na+].O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:12][C:11]([NH2:10])=[O:13])[C:9]([OH:14])=[O:16])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 942335-(4-Hydroxyphenyl)imidazolidine-2,4-dioneHCID 159255Hydroxylamine, sulfate (1:1)

Product 1

HCID 578941alpha-((Aminocarbonyl)amino)-4-hydroxybenzeneacetic acidYield 95%

Reagents, catalysts & solvents 2

HCID 24489
Sodium Dithionite
Catalyst
HCID 962WaterSolvent

Procedure

Crude 5-(p-hydroxyphenyl)hydantoin (85.6 g) is placed in a 1-liter round bottom flask with 41 g hydroxylamine sulfate, 1 g Na2S2O4, 60 g NaOH, and 300 ml H2O. The contents are refluxed for 1 hour and then cooled in an ice bath. Then 125 ml cold concentrated HCl are added. The solids are filtered and washed with 200 ml H2O. The solids are dried in a vacuum oven at 60° C. over the weekend yielding 58.8 g of ca. 95% pure p-hydroxyphenylhydantoic acid (by HPLC analysis).

Workup

  1. temperatureThe contents are refluxed for 1 hour
  2. temperaturecooled in an ice bath
  3. filtrationThe solids are filtered
  4. washwashed with 200 ml H2O
  5. customThe solids are dried in a vacuum oven at 60° C. over the weekend

Sources & evidence

ORD record
ord-41145e644ce04a3eb55d45e91bf58337
Source dataset
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05120855

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes