Sodium Hydroxide → 2,2'-{[(4-Aminophenyl)methyl]azanediyl}diacetic acid

HRID 1755978Notes

Reaction equation

HRID 1755978 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([CH2:8][N:9]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)([O-])=O.[OH-].[Na+]>[Pd].O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][C:11]([OH:13])=[O:12])=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 613945Glycine, N-(carboxymethyl)-N-[(4-nitrophenyl)methyl]-

Product 1

HCID 214604882,2'-{[(4-Aminophenyl)methyl]azanediyl}diacetic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Para-nitrobenzyliminodiacetic acid (1.g, 3.08 nmoles) and Milli-Q® water (55 ml) were combined. The pH of the resultant solution was adjusted to 11.5 by the addition of 10 N NaOH solution. Palladium catalyst (5% palladium on carbon, 700 mg) was added under a hydrogen atmosphere. The reaction mixture was stirred for approximately 6 hours and then filtered through glass sinters and a 0.45 micron Millex filter. The pH of the filtrate was adjusted to below 2 with 1 N HCl and then taken to dryness in vacuo. The residue was dissolved in Milli-Q® water (10 ml) and stored at -70° C. in 1 ml aliquots until further use. Nuclear magnetic resonance confirmed the structure (300 mHz, CDCl3) δ3.268(4H), 3.591(2H); 4.321(2H), 4.741(solvent); 6.822-6.850 (2H); 7.142-7.170 (2H). 13Carbon confirms the structure, δ45.09(1C); 61.05(1 C); 61.153(2C); 119.389 (2C); 131.295 (2C); 131.568 (1C); 148.104 (1C), 176.7 (1C); 181.843 (2C).

Workup

  1. filtrationfiltered through glass sinters
  2. filtrationa 0.45 micron Millex filter
  3. dissolutionThe residue was dissolved in Milli-Q® water (10 ml)
  4. customstored at -70° C. in 1 ml aliquots until further use

Sources & evidence

ORD record
ord-ea4e56c30a2241dcba0f23ecd326dd0a
Source dataset
uspto-grants-1995_08
Patent number
US05439829

Reaction notes

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