Hydrochloric Acid → HCID 87312380, compound

HRID 2421460Notes

Reaction equation

HRID 2421460 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(=O)([O-])[O-].[Na+].[Na+].[N:17]([O-])=O.[Na+].Cl.[CH3:22][N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([CH3:33])([CH3:32])[C:24]1=[CH2:34].[OH-].[Na+]>O.C(O)(=O)C>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([N:1]=[N:17][C:28]2[CH:27]=[C:26]3[C:31](=[CH:30][CH:29]=2)[N:23]([CH3:22])[C:24](=[CH2:34])[C:25]3([CH3:32])[CH3:33])=[CH:3][CH:4]=1)([OH:8])=[O:7]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 9784-Aminobenzoic AcidHCID 83511,3,3-Trimethyl-2-methyleneindolineHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 23668193Sodium Nitrite

Product 1

HCID 87312380HCID 87312380, compoundYield 44.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Procedure

To a cold solution of 10 g (72.9 mmol) of p-aminobezoic acid 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 10.8 g (62.4 mmol) of 1,3,3-trimethyl-2-methyleneindoline 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 7.3 g (31.1%) of azo bezoate (2) as orange solid. TLC Rf 0.26 (chloroform/hexanes/acetone 5:3:2). UV/Vis (methanol) λmax (nm) 455 (ε=32,600 M−1cm−1). ESMS 322.3 [C19H19N3O2 (M+H)+ requires 322.4].

Workup

  1. stirringwith stirring
  2. filtrationThe precipitant was filtered

Sources & evidence

ORD record
ord-466741da922643fc90437bbfa16299ad
Source dataset
uspto-grants-2011_06
Patent number
US07956169B1

Reaction notes

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