Acetic Acid → HCID 71556427, compound

HRID 1497092Notes

Reaction equation

HRID 1497092 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[C:7]3[C:12](=[O:16])[O:13][C:14](=[O:15])[C:6]3=[C:5]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:4]=2[CH:3]=1.[BH4-].[Na+].CC(O)=O>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][OH:16])[C:6]([C:14]([OH:15])=[O:13])=[C:5]2[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 86682927HCID 86682927, compound

Product 1

HCID 71556427HCID 71556427, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-chloro-9-phenylfuro[3,4-b]quinoline-1,3-dione (prepared as described in example 9 step A, 250 mg, 0.81 mmol) in THF was added NaBH4 (30.5 mg, 0.81 mmol) at 15° C., then AcOH (92.4 μl, 1.61 mmol) was added drop wise and stirring was continued for 4 hr at room temperature. The reaction mixture was dissolved in water and the pH was adjusted to ca. 2 and extracted with ethyl acetate. The organic phases were combined and washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified by flash column chromatography, and then further triturated with ether to give the desired product as an off-white solid (25 mg, 10%). MS (ESI): 314 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by flash column chromatography
  7. customfurther triturated with ether

Sources & evidence

ORD record
ord-8da03d30186e42ec92a468cd14f462d9
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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