Water → 3-(Cyclopropylmethoxy)-6-fluoro-8-nitroquinoline

HRID 593352Notes

Reaction equation

HRID 593352 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[N:8]=[CH:7][C:6]([OH:15])=[CH:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:23][CH:24]1[CH2:26][CH2:25]1.O>CS(C)=O>[CH:24]1([CH2:23][O:15][C:6]2[CH:7]=[N:8][C:9]3[C:4]([CH:5]=2)=[CH:3][C:2]([F:1])=[CH:11][C:10]=3[N+:12]([O-:14])=[O:13])[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 681080436-Fluoro-8-nitroquinolin-3-ol

Product 1

HCID 681073683-(Cyclopropylmethoxy)-6-fluoro-8-nitroquinoline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 6-fluoro-8-nitro-quinolin-3-ol (1.285 g, 6.21 mmol) and cesium carbonate (4.046 g, 12.42 mmol) in dimethylsulfoxide (5 ml) was treated with bromomethyl-cyclopropane (1.09 g, 8.1 mmol). After stirring at room temperature overnight water (250 ml) was added and the mixture was extracted with ethyl acetate (2×20 ml) and dichloromethane (2×20 ml). The organic layers were collected, dried and evaporated. The crude product was purified by chromatography on silica gel using a 9:1-mixture of cyclohexane/ethyl acetate as the eluent. 3-Cyclopropylmethoxy-6-fluoro-8-nitro-quinoline was obtained as a yellow solid (600 mg, 45%); (calculated) C13H11FN2O3 [262.2]; (found) [M+H]+=263.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate (2×20 ml) and dichloromethane (2×20 ml)
  3. customThe organic layers were collected
  4. customdried
  5. customevaporated
  6. customThe crude product was purified by chromatography on silica gel using a 9

Sources & evidence

ORD record
ord-4cca9ff875bd4e2fb7e6b9c1ecf37a94
Source dataset
uspto-grants-2016_01
Patent number
US09242943B2

Reaction notes

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