Diphenyl Ether → 7-Chloro-3-methyl-1(2H)-isoquinolinone

HRID 1432851Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]([CH3:15])C(N=[N+]=[N-])=O)=[CH:4][CH:3]=1.C([N:20]([CH2:25]CCC)CCCC)CCC.C1([O:35]C2C=CC=CC=2)C=CC=CC=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:8]=[C:9]([CH3:15])[NH:20][C:25]2=[O:35])=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 7583Diphenyl Ether2×

HCID 7622Tributylamine

HCID 542762533-(4-Chlorophenyl)-2-methyl-acryloyl azide

Product 1

HCID 230846567-Chloro-3-methyl-1(2H)-isoquinolinone

Conditions

Temperature: 50 °C

Procedure

3-(4-Chlorophenyl)-2-methyl-acryloyl azide (11.0 g, 50 mmol) is dissolved in 80 mL of diphenyl ether. The solution is added dropwise to a solution of tributyl amine (11.8 mL, 50 mmol) in 170 mL of diphenyl ether at 210° C. After 4 hours., the solution is cooled 50° C. and diluted with 1.5 L of hexanes. The resulting solid is collected by filtration giving the title compound as a white solid (7.2 g, 37 mmol). 1H NMR (d6-DMSO, 300 MHz) δ11.4 (bs, 1H), 8.02 (s, 1H), 7.67 (d, 1H), 7.55 (d, 1H), 6.34 (s, 1H), 2.18 (s, 3H).

Workup

filtrationThe resulting solid is collected by filtration

Sources & evidence

ORD record: ord-0cccafed5bc64674bc4844feee420d3c
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612075B2

Reaction notes

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