Hydrochloric Acid → HCID 22175702, compound

HRID 1797464Notes

Reaction equation

HRID 1797464 reaction equation
[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([F:16])=[CH:13][CH:14]=2)[C:9](=[O:17])[N:8]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:7]=1[C:23](O)=[O:24])[CH2:2][CH2:3][CH3:4].C(Cl)(=O)C(Cl)=O.[BH4-].[Na+].Cl>O1CCCC1.CN(C)C=O.C(COC)OC>[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([F:16])=[CH:13][CH:14]=2)[C:9](=[O:17])[N:8]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:7]=1[CH2:23][OH:24])[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 4311764Sodium borohydrideHCID 22175341HCID 22175341, compound

Product 1

HCID 22175702HCID 22175702, compoundYield 88.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Butoxy-7-fluoro-2-neopentyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylic acid (2.97 g, 8.5 mmol) was dissolved in tetrahydrofuran (30 ml) and oxalyl chloride (0.9 ml, 10.2 mmol) and N,N-dimethylformamide (2 drops) were added thereto. The mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in tetrahydrofuran (20 ml). The obtained solution was added dropwise to sodium tetrahydroborate (1.13 g, 30 mmol) in dimethoxyethane (20 ml) at 0° C. The obtained mixture was stirred at 0° C. for 1 h. The reaction mixture was poured into 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained crystals were recrystallized from tetrahydrofuran-diisopropyl ether to give 4-butoxy-7-fluoro-3-hydroxymethyl-2-neopentyl-1(2H)-isoquinolinone (2.52 g, 88.4%) as crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in tetrahydrofuran (20 ml)
  3. stirringThe obtained mixture was stirred at 0° C. for 1 h
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained crystals were recrystallized from tetrahydrofuran-diisopropyl ether

Sources & evidence

ORD record
ord-859f42f7ab61446fa9c0c84df4c10c5d
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

Loading…