Sulfuric Acid → HCID 86723684, compound

HRID 577446Notes

Reaction equation

HRID 577446 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][CH3:12].CN(C(O[N:21]1N=N[C:23]2C=CC=N[C:22]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.COC(OC)CN.OS(O)(=O)=O.[OH-].[Na+]>S1(CCCC1)(=O)=O>[F:1][C:2]1[CH:10]=[C:9]2[C:5](=[CH:4][C:3]=1[O:11][CH3:12])[C:6](=[O:8])[NH:21][CH:22]=[CH:23]2

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 89728Aminoacetaldehyde dimethyl acetalHCID 5984364-Fluoro-3-methoxybenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86723684HCID 86723684, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

A solution of 4-fluoro-3-methoxybenzoic acid (1.30 g, 7.64 mmol) and TEA (1.25 mL, 8.97 mmol) in sulfolane (6.0 mL) was treated with HATU (3.25 g, 8.55 mmol). After 10 minutes, aminoacetaldehyde dimethylacetal (0.925 mL, 8.58 mmol) was added. The reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was then treated with conc. H2SO4 (15 mL) and stirred at 60° C. for 2 days. The reaction mixture was poured over ice and brought to pH˜4 with 10M NaOH (˜55 mL). The precipitate was collected by filtration, washed with water, and dried under vacuum to give 6-fluoro-7-methoxyisoquinolin-1(2H)-one (Cpd L, 1.32 g, 89%) as a white powder.

Workup

  1. stirringstirred at 60° C. for 2 days
  2. additionThe reaction mixture was poured over ice
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-fdb5560e7aab40d19ff9338fd477821a
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

Loading…