Sodium Nitrite → 3-Hydrazino-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester

HRID 2092633Notes

Reaction equation

HRID 2092633 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=2)[CH:7]=[C:6]([NH2:17])[CH:5]=1.[N:19]([O-])=O.[Na+]>Cl.O>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=2)[CH:7]=[C:6]([NH:17][NH2:19])[CH:5]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 57851018Methyl 3-amino-5-(5-methylpyridin-2-yl)benzoate

Product 1

HCID 577707543-Hydrazino-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl esterYield 174.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

3-Amino-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester (1.0 g, 4 mmol) was suspended in 16 mL concentrated aqueous HCl, and the mixture was cooled to 0° C. A solution of sodium nitrite (0.30 g) in water (3 mL) was added, and the mixture was stirred at 0° C. for 45 minutes. A solution of SnCl2 hydrate (2.34 g) in 5 mL concentrated aqueous HCl was then added. The reaction mixture was stirred for one hour at room temperature, then filtered. The collected solid was washed with water and dried to give 1.80 g of 3-hydrazino-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester as a white powder.

Workup

  1. stirringThe reaction mixture was stirred for one hour at room temperature
  2. filtrationfiltered
  3. washThe collected solid was washed with water
  4. customdried

Sources & evidence

ORD record
ord-70db762fd4bb44748d30b966ee70be97
Source dataset
uspto-grants-2013_05
Patent number
US08440708B2

Reaction notes

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