2-Methyl-2-butene → HCID 89543691, compound

HRID 922787Notes

Reaction equation

HRID 922787 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([CH:18]=[O:19])=[CH:15][CH:16]=3)[N:11]=[C:10]([C:20]([NH2:22])=[O:21])[CH:9]=2)=[CH:4][CH:3]=1.CC(=CC)C.Cl([O-])=[O:29].[Na+].O.P([O-])(O)(O)=O.[Na+]>CC(O)(C)C.O>[NH2:22][C:20]([C:10]1[CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:17]2[C:12](=[CH:13][C:14]([C:18]([OH:29])=[O:19])=[CH:15][CH:16]=2)[N:11]=1)=[O:21]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 89543658HCID 89543658, compound

Product 1

HCID 89543691HCID 89543691, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of 4-(4-fluorophenyl)-7-formylquinoline-2-carboxamide (5-2, 200.0 mg, 0.680 mmol, 1.0 equiv.) and 2-methyl-2-butene (3.96 mL, 37.4 mmol, 55 equiv.) in t-BuOH (14.0 mL, 0.05 M) was added a solution of sodium chlorite (553.0 mg, 6.12 mmol, 9 equiv.) and sodium dihydrogen phosphate monohydrate (559.0 mg, 4.08 mmol, 6 equiv.) in water (6.5 mL). The resulting mixture was stirred at room temperature for 1 hour. A white solid precipitated. Water (100.0 ml) was added and the mixture stirred for 30 minutes. The solid was collected via suction filtration, washed with water, dried in vacuo to give 2-(aminocarbonyl)-4-(4-fluorophenyl)quinoline-7-carboxylic acid (5-3, 150.0 mg, 71.1%) as a white solid. LRMS m/z (M+H)+ 311.1 found, 311.1 required.

Workup

  1. customA white solid precipitated
  2. additionWater (100.0 ml) was added
  3. stirringthe mixture stirred for 30 minutes
  4. filtrationThe solid was collected via suction filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a702d1c4efbb4eb5aa392eaf2bcb98b1
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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