Hydrochloric Acid → HCID 117780376, compound

HRID 520316Notes

Reaction equation

[F:1][CH:2]([F:23])[O:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([F:14])[CH:13]=1)[C:10](=[O:15])[N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]2.Cl>>[F:23][CH:2]([F:1])[O:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([F:14])[CH:13]=1)[C:10](=[O:15])[NH:9][CH2:8][CH2:7]2

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 117802897HCID 117802897, compound

Product 1

HCID 117780376HCID 117780376, compoundYield 144.2%

Procedure

To a mixture of 144i (2.0 g, 6.0 mmol) in EtOAC (10 mL) was added HCl in EtOAC (20 mL, 4 M) at RT. See FIG. 3. The reaction mixture was stirred at room temperature for 1 h and then concentrated under reduced pressure. The crude residue was triturated with MTBE (20 mL) to give 2.0 g (85.9%) of 6-(difluoromethoxy)-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one 144j. 1H NMR (400 MHz, CDCl3) δ 6.80-6.85 (m, 2H), 6.40-6.76 (m, 1H), 6.19 (s, 1H), 3.51-3.55 (m, 2H), 2.98-3.01 (m, 2H); MS-ESI [M+H]+=232.0.

Workup

concentrationconcentrated under reduced pressure
customThe crude residue was triturated with MTBE (20 mL)

Sources & evidence

ORD record: ord-53477fc2bfc549db819f7ac1a202dc50
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326985B2

Reaction notes

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