3-Fluoroaniline → HCID 9905447, compound

HRID 1987491Notes

Reaction equation

HRID 1987491 reaction equation
Cl[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][C:6]([O:15][CH2:16][CH3:17])=[C:7]([O:12][CH2:13][CH3:14])[CH:8]=2)[N:3]=1.[F:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22]>>[F:18][C:19]1[CH:20]=[C:21]([NH:22][C:2]2[CH:11]=[N:10][C:9]3[C:4](=[CH:5][C:6]([O:15][CH2:16][CH3:17])=[C:7]([O:12][CH2:13][CH3:14])[CH:8]=3)[N:3]=2)[CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 97423-FluoroanilineHCID 12043216HCID 12043216, compound

Product 1

HCID 9905447HCID 9905447, compoundYield 54.1%

Procedure

To 0.25 g (0.989 mmol) of 2-chloro-6,7-diethoxyquinoxaline is added 2 mL of m-fluoroaniline. This mixture is heated under nitrogen overnight to 120° C. The resulting mixture is chromatographed (30:1 CH2Cl2: EtOH) to yield partially purified product. This solid is triturated with ethyl acetate to give 0.175 g of the product as a brownish yellow solid in 54.1% yield (m.p. 193° C.). Anal. Calcd for C18H18N3O2F.0.25H2O: C, 65.15; H, 5.62; N, 12.66. Found: C, 65.30; H, 5.30; N, 12.41.

Workup

  1. temperatureThis mixture is heated under nitrogen overnight to 120° C
  2. customThe resulting mixture is chromatographed (30:1 CH2Cl2: EtOH)
  3. customto yield partially purified product
  4. customThis solid is triturated with ethyl acetate

Sources & evidence

ORD record
ord-3611aa392fb24784aee6d12b5c89234c
Source dataset
uspto-grants-2009_06
Patent number
US07550597B2

Reaction notes

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