Hydrochloric Acid → HCID 86677185, compound

HRID 929365Notes

Reaction equation

HRID 929365 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(=O)C(C)(C)C)=[CH:4][C:3]=1[C:15]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][CH:21]=[N:20]2)=[O:16].Cl.[OH-].[Na+]>CC(O)=O>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[CH:22][CH:21]=[N:20]3)=[O:16])[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71268616N-(4-fluoro-3-(quinoxaline-6-carbonyl)phenyl)pivalamide

Product 1

HCID 86677185HCID 86677185, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of N-(4-fluoro-3-(quinoxaline-6-carbonyl)phenyl)pivalamide (4.7 g, 13.5 mmol, 1.0 eq.) in HOAc (60 mL) was added cone. HCl (30 mL). The mixture was stirred at 110° C. for 4 h, then poured onto ice. The mixture was basified to pH=10 by the addition of 1N NaOH aqueous solution and extracted with DCM (100 mL×3). The combined organic layers were dried over Na2SO4 and concentrated. The resulting residue was purified by flash column chromatography (PE/EA=1/2, v/v) to afford (5-amino-2-fluorophenyl)(quinoxalin-6-yl)methanone (3.5 g, 99%) which was used in the next step without further purification.

Workup

  1. additionpoured onto ice
  2. extractionextracted with DCM (100 mL×3)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified by flash column chromatography (PE/EA=1/2

Sources & evidence

ORD record
ord-e7b94c1df2c846bd9e4d226ef4985a2d
Source dataset
uspto-grants-2016_03
Patent number
US09295671B2

Reaction notes

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