Stannous chloride dihydrate → HCID 89602403, compound

HRID 869066Notes

Reaction equation

HRID 869066 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[CH3:14].O.O.[Sn](Cl)[Cl:18]>O.Cl>[ClH:18].[NH:5]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[CH3:14])[NH2:1]

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 70103164-Amino-3-methylbenzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 89602403HCID 89602403, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

A solution of sodium nitrite (0.52 g, 7.57 mmol) in water (3 mL) was added dropwise to a cold (0° C.) mixture of 4-amino-3-methylbenzonitrile (1 g, 7.57 mmol) and concentrated HCl (12 mL) keeping the internal temperature below 0° C. After 5 min stirring, tin dichloride dihydrate (3.75 g, 16.6 mmol) in concentrated HCl (4 mL) was added at 0° C. The reaction mixture was allowed to warm to rt and stirred for 2 h. The resulting precipitate was collected by vacuum filtration and dried to provide 500 mg of the title compound. tR: 0.24 min (LC-MS 2); ESI-MS: 148 [M+H]+ (LC-MS 2).

Workup

  1. customthe internal temperature below 0° C
  2. stirringstirred for 2 h
  3. filtrationThe resulting precipitate was collected by vacuum filtration
  4. customdried

Sources & evidence

ORD record
ord-bab27d06435a441fa550afe040ef18ee
Source dataset
uspto-grants-2015_03
Patent number
US08969341B2

Reaction notes

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