Acetic Acid → HCID 87312636, compound

HRID 2421461Notes

Reaction equation

HRID 2421461 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11](=[O:14])([O-])[O-].[Na+].[Na+].[N:17]([O-])=O.[Na+].Cl.CO[N:24](OC)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[OH-].[Na+].[C:35]([OH:38])(=O)C>O>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([N:1]=[N:17][C:28]2[C:27]([O:38][CH3:35])=[CH:26][C:25]([NH2:24])=[C:30]([O:14][CH3:11])[CH:29]=2)=[CH:3][CH:4]=1)([OH:8])=[O:7]

Participants

9

Reactant 7

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 9784-Aminobenzoic AcidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 20367079HCID 20367079, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 87312636HCID 87312636, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a cold solution of 10 g (72.9 mmol) of p-aminobezoic acid (3) and 2.4 g (22.6 mmol) of sodium carbonate in 100 mL of DI water was added a solution of 3.5 g (50.7 mmol) of NaNO2 in 10 mL of DI water at 15° C. with stirring. The above mixture was poured into a mixture of 10 mL of concentrated HCl and 60 gm of crashed ice with stirring. Then of 11.2 g (73.2 mmol) of dimethoxyaniline (7) and 6 ml of acetic acid were added to the reaction mixture. After 10 min the reaction mixture was neutralized with 8 mL of 20% NaOH solution in water. The precipitant was filtered. Flash chromatography with chloroform/hexanes/acetone 5:3:2 mobile system provided 16 g (72.7%) of azo bezoate (8) as orange solid. TLC Rf 0.33 (1:9 MeOH-DCM). UV/Vis (methanol) λmax (nm) 450 (ε=31,800 M−1cm−1). 1H NMR (DMSO/D2O) δ 3.76 (s, 3H), 3.84 (s, 3H), 6.45 (s, 1H), 7.25 (s, 1H), 7.69 (d, 2H, J=8.4 Hz), 8.00 (d, 2H, J=8.4 Hz). ESMS 302.3 [C15H15N3O4 (M+H)+ requires 302.3].

Workup

  1. stirringwith stirring
  2. filtrationThe precipitant was filtered

Sources & evidence

ORD record
ord-b99c7ec945b84a28a0184b9df468e54f
Source dataset
uspto-grants-2011_06
Patent number
US07956169B1

Reaction notes

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