HCID 68295580, compound → HCID 86700715, compound

HRID 572473Notes

Reaction equation

HRID 572473 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[N:11]([CH3:20])[C:10]=2[CH2:21][OH:22])[CH:5]=[CH:6][C:7]=1[F:8]>C(Cl)(Cl)Cl.O=[Mn]=O>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[N:11]([CH3:20])[C:10]=2[CH:21]=[O:22])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 1

HCID 68295580HCID 68295580, compound

Product 1

HCID 86700715HCID 86700715, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-(3,4-Difluoro-phenyl)-3-hydroxymethyl-2-methyl-2H-isoquinolin-1-one (500 mg, 1.66 mmol) in CHCl3 (10 ml) was added MnO2 (1.87 g, 21.6 mmol). The reaction mixture was stirred at 70° C. overnight under N2. TLC showed SM was consumed, cooled to RT, the reaction mixture was filtered, and the filtrate was concentrated to dryness to afford title product which was used for the next step directly. (m=460.0 mg, yield=92.6%.) 1HNMR: (400 MHz, d6-DMSO) δ 3.89 (s, 3H), 7.09 (t, J=6.0 Hz, 1H), 7.15 (d, J=6.8 Hz, 1H), 7.24 (m, 1H), 7.36 (dd, J1=9.6 Hz, J2=15.6 Hz, 1H), 7.55 (m, 2H), 8.55 (d, J=8.0 Hz, 1H), 9.61 (s, 1H).

Workup

  1. customwas consumed
  2. temperaturecooled to RT
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-c0e579e64c4c4ba3890282cc75ab7d22
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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