Stannous Chloride → 252752-46-8

HRID 612342Notes

Reaction equation

HRID 612342 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[N:13]([O-])=O.[Na+].[Cl:17][Sn]Cl>Cl.O>[ClH:17].[NH:1]([C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1)[NH2:13]

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 2761030Methyl 2-(4-aminophenyl)acetateHCID 23668193Sodium Nitrite

Product 1

HCID 19593944252752-46-8Yield 69.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a solution of methyl 4-aminophenylacetate (5.5 g, 33.3 mmol) in concentrated HCl (35 mL) at 0° C. is added a solution of NaNO2 (2.3 g, 33.3 mmol) in water (10 mL). The temperature of the reaction is maintained at 0-5° C. After stirring for 30 minutes, a solution of SnCl2 (19 g, 99.9 mmol) in concentrated HCl (10 mL) is added and the mixture is vigorously stirred with a stirring rod. The mixture is then diluted with water (50 mL), and the resulting precipitate is collected by suction filtration and washed with water. The solid is dried under vacuum to give 5 g of 18, which is used without further purification.

Workup

  1. stirringthe mixture is vigorously stirred with a stirring rod
  2. filtrationthe resulting precipitate is collected by suction filtration
  3. washwashed with water
  4. customThe solid is dried under vacuum

Sources & evidence

ORD record
ord-507f2ffd486e4ce1927227d526c2bc5b
Source dataset
uspto-grants-1999_12
Patent number
US06004536

Reaction notes

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