Hydrochloric Acid → HCID 10038811, compound

HRID 422023Notes

Reaction equation

HRID 422023 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].C(=O)([O-])[O-].[K+].[K+].F[C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25].Cl>CN(C=O)C>[CH3:6][O:5][C:3](=[O:4])[CH:2]([C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25])[C:1]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7943Dimethyl malonateHCID 11430Potassium CarbonateHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 10038811HCID 10038811, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of dimethyl malonate (6.24 g, 46.7 mmol) and potassium carbonate (6.51 g, 47.2 mmol) in DMF (20 ml) is added 2,4-difluoronitrobenzene (5.00 g, 30.8 mmol). The reaction is stirred at room temperature for 1 hour and then is brought to 60° C. After stirring for 1 hour, it is cooled to room temperature and 1 N HCl (100 ml) is added. The mixture is extracted with ethyl acetate (80 ml×2). The organic layers are combined, dried and concentrated. The desired compound is obtained after flash column chromatography purification (silica gel, eluted with hexanes-ethyl acetate): 1H NMR (CDCl3) δ 3.82 (s, 6H), 5.40 (s, 1H), 7.18-7.26 (m, 21), 8.16 (dd, 1H, J1=4.8 Hz, J2=8.8 Hz); LC-MS: 272.1 (MH+).

Workup

  1. customis brought to 60° C
  2. stirringAfter stirring for 1 hour
  3. temperatureit is cooled to room temperature
  4. extractionThe mixture is extracted with ethyl acetate (80 ml×2)
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2495f12a134c42a68dcdb7338f364ce4
Source dataset
uspto-grants-2012_01
Patent number
US08101608B2

Reaction notes

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