Potassium Carbonate → HCID 59402698, compound

HRID 415598Notes

Reaction equation

HRID 415598 reaction equation
[F:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].CN(C=O)C.Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+]>>[F:1][C:2]1[C:10]([O:11][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 451190962-Fluoro-3-hydroxybenzamideHCID 86643273HCID 86643273, compound

Product 1

HCID 59402698HCID 59402698, compound

Conditions

Temperature
90 °C

Procedure

To the solution of 2-fluoro-3-Hydroxy-benzamide (0.12 g, 0.774 mmol) in 20 mL DMF 1-bromohexane (0.13 mL, 1.0 mmol), Potassium Carbonate (0.213, 1.4 mmol) was added. The reaction mixture was stirred at 90° C. for 4 h. DMF was distilled off and the reaction mixture was extracted with EtOAc. The obtained crude compound was purified by column chromatography on silica (230-400μ) using ethyl acetate/hexane (50:50) as the eluent to provide the title compound. (0.05 g, 28%). 1H NMR (DMSO-d6, 400 MHz with D2O): δ 0.82-0.99 (m, 3H), 1.10-1.33 (m, 6H), 1.67-1.71 (m, 2H), 3.99-4.15 (t, 2H, J=8.0 Hz), 7.08-7.24 (m, 2H). MS ES+ (214.33), HPLC (method 6) Rt=11.15 min.

Workup

  1. distillationDMF was distilled off
  2. extractionthe reaction mixture was extracted with EtOAc
  3. customThe obtained crude compound
  4. customwas purified by column chromatography on silica (230-400μ)

Sources & evidence

ORD record
ord-ceb56a7d460449639dcb9ee09a0f7d70
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

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