Hydrochloric Acid → HCID 87312933, compound

HRID 2421462Notes

Reaction equation

HRID 2421462 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N:11][C:12]2[C:18]([O:19][CH3:20])=[CH:17][C:15]([NH2:16])=[C:14]([O:21][CH3:22])[CH:13]=2)=[CH:6][CH:5]=1)([OH:3])=[O:2].C(=O)([O-])[O-].[Na+].[Na+].[N:29]([O-])=O.[Na+].Cl.[CH3:34][N:35]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:37]([CH3:45])([CH3:44])[C:36]1=[CH2:46].[OH-].[Na+]>O.C(O)(=O)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]=[N:11][C:12]2[C:18]([O:19][CH3:20])=[CH:17][C:15]([N:16]=[N:29][C:40]3[CH:39]=[C:38]4[C:43](=[CH:42][CH:41]=3)[N:35]([CH3:34])[C:36](=[CH2:46])[C:37]4([CH3:44])[CH3:45])=[C:14]([O:21][CH3:22])[CH:13]=2)=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 83511,3,3-Trimethyl-2-methyleneindolineHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 87312636HCID 87312636, compound

Product 1

HCID 87312933HCID 87312933, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Procedure

To a cold solution of 5 g (16.6 mmol) of 4-(4-carboxy-phenylazo)-2,5-dimethoxyaniline (8) and 1.25 g (11.8 mmol) of sodium carbonate in 50 mL of DI water was added a solution of 1.75 g (25.4 mmol) of NaNO2 in 5 mL of DI water at 15° C. with stirring. The above mixture was poured into a mixture of 5 mL of concentrated HCl and 30 gm of crashed ice with stirring. Then of 2.9 g (16.6 mmol) of 1,3,3-trimethyl-2-methyleneindoline and 1.5 ml of acetic acid were added to the reaction mixture. After 10 min the reaction mixture was neutralized with 6 mL of 20% NaOH solution in water. The precipitant was filtered. Flash chromatography with chloroform/hexanes/acetone 5:3:2 mobile system provided 5.5 g (68.2%) of azo bezoate (9) as dark blue solid. TLC Rf 0.48 (1:9 MeOH-DCM). UV/Vis (buffer pH=11) λmax (nm) 585 (ε=48,500 M−1cm−1). 486.6 [C27H27N5O4 (M+H)+ requires 486.5].

Workup

  1. stirringwith stirring
  2. filtrationThe precipitant was filtered

Sources & evidence

ORD record
ord-379a547e31734097929405986ac3b0ad
Source dataset
uspto-grants-2011_06
Patent number
US07956169B1

Reaction notes

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