Hydrochloric Acid → HCID 57991948, compound

HRID 1051382Notes

Reaction equation

HRID 1051382 reaction equation
[F:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]([O:14]C)=[O:13])=[CH:7][CH:6]=2.[Li+].[OH-].Cl>C1COCC1.O>[F:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 67089276HCID 67089276, compound

Product 1

HCID 57991948HCID 57991948, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A slurry of 88 (413 mg, 2.013 mmol) and LiOH (56 mg, 2.34 mmol) in THF (9.8 mL) and water (1.5 mL) was stirred at RT for 1.5 h. An additional 50 mg of LiOH was added (total: 106 mg, 4.43 mmol), and the reaction was stirred for an additional 2 h. The THF was removed on a rotary evaporator. The reaction mixture was suspended in water (10 mL) and treated with 10M HCl in water (0.604 mL, 6.04 mmol). A white cloudy precipitate was collected by vacuum filtration. The precipitate was washed with water (2×2 mL) and dried under house vacuum over night to afford 349 mg (100%) of 3-fluoroisoquinoline-6-carboxylic acid (90) as a white solid, which was used in the next step without further purification.

Workup

  1. customThe THF was removed on a rotary evaporator
  2. filtrationA white cloudy precipitate was collected by vacuum filtration
  3. washThe precipitate was washed with water (2×2 mL)
  4. customdried under house vacuum over night

Sources & evidence

ORD record
ord-2dccaab51a724cc5ac0756bb229ffa86
Source dataset
uspto-grants-2016_07
Patent number
US09388171B2

Reaction notes

Loading…