Dichloromethane → 3-Difluoromethoxy-8-nitro-quinoline

HRID 593348Notes

Reaction equation

HRID 593348 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][C:10]([OH:14])=[CH:9]2)([O-:3])=[O:2].Cl[C:16]([F:21])([F:20])C([O-])=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+].ClCCl>CN(C)C=O>[F:20][CH:16]([F:21])[O:14][C:10]1[CH:11]=[N:12][C:13]2[C:8]([CH:9]=1)=[CH:7][CH:6]=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 2734985Sodium chlorodifluoroacetateHCID 543669748-Nitro-3-quinolinol

Product 1

HCID 681078853-Difluoromethoxy-8-nitro-quinolineYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 8-nitro-quinolin-3-ol (CAS25369-37-3) (500 mg, 2.63 mmol) in dimethylformamide (5 ml) was treated with sodium chlorodifluoroacetate (481 mg, 3.15 mmol). The mixture was heated to 100° C. overnight under a nitrogen atmosphere. For the workup, the reaction mixture was cooled to room temperature, then saturated aqueous sodium carbonate solution and dichloromethane were added. The organic layer was separated, dried over sodium sulphate, then evaporated. The crude product was purified by chromatography on silica gel using a gradient of cyclohexane/ethyl acetate=9:1 to 8:1 as the eluent yielding 100 mg (16%) of the 3-difluoromethoxy-8-nitro-quinoline as a yellow solid; (calculated) C10H6F2N2O3 [240.2]; (found) [M+H]+=241.

Workup

  1. temperatureFor the workup, the reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customThe crude product was purified by chromatography on silica gel using a gradient of cyclohexane/ethyl acetate=9:1 to 8:1 as the eluent

Sources & evidence

ORD record
ord-fe05429b5cf541c390a11dd38dc7a5de
Source dataset
uspto-grants-2016_01
Patent number
US09242943B2

Reaction notes

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