Stannous chloride dihydrate → 6-Hydrazino-4-trifluoromethylquinolin-2(1H)-one

HRID 642845Notes

Reaction equation

HRID 642845 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[C:5]2[C:13]([F:16])([F:15])[F:14].[N:17]([O-])=O.[Na+].O.O.Cl[Sn]Cl>Cl.O>[NH:1]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[C:5]2[C:13]([F:16])([F:14])[F:15])[NH2:17]

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 160903086-amino-4-trifluoromethylquinolin-2(1H)-oneHCID 23668193Sodium Nitrite

Product 1

HCID 98995846-Hydrazino-4-trifluoromethylquinolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
-1 °C

Procedure

In a 250 mL rb flask a suspension of Compound 200 (structure 3 of Scheme XXXIII) (2.28 g, 10 mmol) in 10 mL conc. HCl was cooled to −1° C. and a solution of NaNO2 (0.40 g, 12 mmol) in water (5 mL) was added dropwise in 20 min. The dark yellow suspension was stirred at −1° C. for 1 h and then a solution of SnCl2.2H2O (5.2 g, 15 mmol) in conc HCl (10 mL) was added dropwise in 10 min. The light yellow suspension of Compound 793 was stirred at −1° C. for 2 h and then used directly or kept in a refrigerator at −1° C. until it was used (the crude compound can be stored for at least one month without decomposition).

Workup

  1. stirringwas stirred at −1° C. for 2 h
  2. customkept in a refrigerator at −1° C. until it
  3. waitcan be stored for at least one month without decomposition

Sources & evidence

ORD record
ord-2bc6a1d0758f4b95a3b0ebaaa02df2e1
Source dataset
uspto-grants-2010_04
Patent number
US07696246B2

Reaction notes

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