Methyl 4-aminobenzoate → HCID 178499563, compound

HRID 1367874Notes

Reaction equation

HRID 1367874 reaction equation
[N:1]([O-])=O.[Na+].[CH3:5][O:6][C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1.Cl.[CH3:17][O:18][C:19](=[O:26])[CH2:20][C:21]1[N:22]=[CH:23][NH:24][CH:25]=1>Cl.B([O-])([O-])[O-].B([O-])([O-])[O-].B([O-])([O-])[O-].B([O-])([O-])[O-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]>[CH3:5][O:6][C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([N:14]=[N:1][C:23]2[NH:24][CH:25]=[C:21]([CH2:20][C:19]([O:18][CH3:17])=[O:26])[N:22]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 12082Methyl 4-aminobenzoateHCID 23668193Sodium NitriteHCID 178499561HCID 178499561, compound

Product 1

HCID 178499563HCID 178499563, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21225931Dodecasodium;tetraborateSolvent

Conditions

Temperature
0 °C

Procedure

An aqueous solution (5.1 mL) of sodium nitrite (4.5 mmol, 311 mg) was cooled in an ice bath and added to a mixture of 694 mg (4.5 mmol) of 4-amino-benzoic acid methyl ester in 2.36 N aq. HCl (7.5 mL) at 0° C. The mixture was stirred at 0° C. for 30 min, and the reaction mixture was added to a mixture of 795 mg (4.5 mmol) of (1H-imidazol-4-yl)-acetic acid methyl ester hydrochloride in saturated aqueous sodium tetraborate solution (150 mL). The mixture was stirred at 0° C. for 1.5 h and slowly warmed up to room temperature. The 4-(4-Methoxycarbonylmethyl-1H-imidazol-2-ylazo)-benzoic acid methyl ester was obtained after filtering and washing with water in a quantitative yield. LCMS: 303 (M+1)+.

Workup

  1. stirringThe mixture was stirred at 0° C. for 1.5 h
  2. temperatureslowly warmed up to room temperature

Sources & evidence

ORD record
ord-34af99be187944b3b3e3b8472c332ebe
Source dataset
uspto-grants-2011_02
Patent number
US07893267B2

Reaction notes

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